{"id":"https://openalex.org/W2066322500","doi":"https://doi.org/10.1021/ol9010757","title":"Synthesis of 1,3-Amino Alcohol Derivatives via a Silicon-Mediated Ring-Opening of Substituted Piperidines","display_name":"Synthesis of 1,3-Amino Alcohol Derivatives via a Silicon-Mediated Ring-Opening of Substituted Piperidines","publication_year":2009,"publication_date":"2009-06-11","ids":{"openalex":"https://openalex.org/W2066322500","doi":"https://doi.org/10.1021/ol9010757","mag":"2066322500","pmid":"https://pubmed.ncbi.nlm.nih.gov/19552467"},"language":"en","primary_location":{"id":"doi:10.1021/ol9010757","doi":"https://doi.org/10.1021/ol9010757","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol9010757","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5079976634","display_name":"W. Stephen McCall","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"W. Stephen McCall","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]},{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5077943087","display_name":"Daniel L. Comins","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Daniel L. Comins","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204","institution_ids":["https://openalex.org/I137902535"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5077943087"],"corresponding_institution_ids":["https://openalex.org/I137902535"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.4563,"has_fulltext":false,"cited_by_count":14,"citation_normalized_percentile":{"value":0.59396952,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":97},"biblio":{"volume":"11","issue":"13","first_page":"2940","last_page":"2942"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.7339000105857849,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.7339000105857849,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.13439999520778656,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.07980000227689743,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/1-3-amino-alcohols","display_name":"1,3-amino alcohols","score":0.9670000076293945},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.7850000262260437},{"id":"https://openalex.org/keywords/tetrabutylammonium-fluoride","display_name":"tetrabutylammonium fluoride","score":0.8600000143051147},{"id":"https://openalex.org/keywords/cyanogen-bromide","display_name":"cyanogen bromide","score":0.996999979019165},{"id":"https://openalex.org/keywords/cyanamide","display_name":"cyanamide","score":0.7110000252723694},{"id":"https://openalex.org/keywords/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.9440000057220459},{"id":"https://openalex.org/keywords/alkylamines","display_name":"alkylamines","score":0.6830000281333923},{"id":"https://openalex.org/keywords/chiral-centers","display_name":"stereogenic centers","score":0.6830000281333923}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9418119192123413},{"id":"https://openalex.org/C2779606280","wikidata":"https://www.wikidata.org/wiki/Q414555","display_name":"Cyanamide","level":2,"score":0.8087612390518188},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.7179994583129883},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.6618974804878235},{"id":"https://openalex.org/C2781066024","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Alcohol","level":2,"score":0.6495627164840698},{"id":"https://openalex.org/C2777093645","wikidata":"https://www.wikidata.org/wiki/Q420258","display_name":"Cyanogen bromide","level":4,"score":0.5817350149154663},{"id":"https://openalex.org/C2776254738","wikidata":"https://www.wikidata.org/wiki/Q81406","display_name":"Alkene","level":3,"score":0.5464557409286499},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4705626964569092},{"id":"https://openalex.org/C2776300020","wikidata":"https://www.wikidata.org/wiki/Q422423","display_name":"Bromide","level":2,"score":0.4614502191543579},{"id":"https://openalex.org/C2778675482","wikidata":"https://www.wikidata.org/wiki/Q223062","display_name":"Allyl bromide","level":2,"score":0.4491833448410034},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.37974244356155396},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3422545790672302},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.10631957650184631},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0},{"id":"https://openalex.org/C167625842","wikidata":"https://www.wikidata.org/wiki/Q899763","display_name":"Peptide sequence","level":3,"score":0.0}],"mesh":[{"descriptor_ui":"D000605","descriptor_name":"Amino Alcohols","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000605","descriptor_name":"Amino Alcohols","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D003488","descriptor_name":"Cyanogen Bromide","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010880","descriptor_name":"Piperidines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D014297","descriptor_name":"Trimethylsilyl Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ol9010757","doi":"https://doi.org/10.1021/ol9010757","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol9010757","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:19552467","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/19552467","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1902379259","display_name":"SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYLDIHYDROPYRIDINE","funder_award_id":"R01GM034442","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":17,"referenced_works":["https://openalex.org/W170487507","https://openalex.org/W1972425544","https://openalex.org/W1984451439","https://openalex.org/W1996892864","https://openalex.org/W2003025773","https://openalex.org/W2014923810","https://openalex.org/W2069603008","https://openalex.org/W2094454175","https://openalex.org/W2095086594","https://openalex.org/W2119343165","https://openalex.org/W2120400560","https://openalex.org/W2155004640","https://openalex.org/W2160302986","https://openalex.org/W2170733288","https://openalex.org/W2949633107","https://openalex.org/W2950916249","https://openalex.org/W2952482483"],"related_works":["https://openalex.org/W1972425544","https://openalex.org/W2094454175","https://openalex.org/W2949769831","https://openalex.org/W2953033659","https://openalex.org/W2132786166","https://openalex.org/W2066001395","https://openalex.org/W2024278921","https://openalex.org/W2329672204","https://openalex.org/W2953214616","https://openalex.org/W2091468801"],"abstract_inverted_index":{"Multisubstituted":[0],"piperidines":[1],"containing":[2,40],"a":[3],"trimethylsilylmethyl":[4],"group":[5],"at":[6],"C-2":[7],"can":[8],"be":[9],"opened":[10],"regioselectively":[11],"with":[12],"TBAF":[13],"and":[14,24],"cyanogen":[15],"bromide.":[16],"The":[17],"ring-opened":[18],"products":[19],"contain":[20],"synthetically":[21],"useful":[22,32],"cyanamide":[23],"terminal":[25],"alkene":[26],"functional":[27],"groups.":[28],"This":[29],"method":[30],"is":[31],"for":[33],"the":[34],"stereoselective":[35],"synthesis":[36],"of":[37],"alkylamine":[38],"derivatives":[39],"multiple":[41],"chiral":[42],"centers.":[43]},"counts_by_year":[{"year":2023,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":3},{"year":2012,"cited_by_count":2}],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2016-06-24T00:00:00"}
