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Enantioselective Synthesis of α-Amino Nitriles from N-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as Catalyst
A novel catalytic enantioselective Strecker synthesis of chiral α-amino nitriles and α-amino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity. Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as cat...
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Published in: | Organic letters 1999-07, Vol.1 (1), p.157-160 |
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container_title | Organic letters |
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creator | Corey, E. J Grogan, Michael J |
description | A novel catalytic enantioselective Strecker synthesis of chiral α-amino nitriles and α-amino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity. Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as catalyst and (2) the use of the N-benzhydryl substituent on the imine substrate. |
doi_str_mv | 10.1021/ol990623l |
format | article |
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Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as catalyst and (2) the use of the N-benzhydryl substituent on the imine substrate.</description><subject>Benzhydryl Compounds - chemical synthesis</subject><subject>Bridged Bicyclo Compounds - chemistry</subject><subject>Catalysis</subject><subject>Guanidines - chemistry</subject><subject>Hydrogen Cyanide - chemistry</subject><subject>Imines - chemical synthesis</subject><subject>Models, Molecular</subject><subject>Nitriles - chemical synthesis</subject><subject>Schiff Bases</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNpt0L1OwzAQB3ALgSgUBl4AeWFgCNgOTvDYRqWtVJWB7pHjD8WVk1S2CwoSD8WL8EwYBVUMTHe6--l0-gNwhdEdRgTfd5YxlJHUHoEzTEma5IiS40OfoRE4936LEI4TdgpGGD0SQik5Ax-zlrfBdF5ZJYJ5VfClb0OtvPGw0_DrM5k0pu3g2gRnrPJQu66B62Sq2ve6l663cBlBXPBWwkWxhm8m1JDDojaOWzg1ohfWCDjf89bIKCH3sOCB296HC3CiufXq8reOweZptikWyep5viwmq4SnGIeEiQeBBWWScISRYFWuKaO5pCLDaVZlpCKYVTiXqcYVYzKPlCtCkdYqQyIdg9vhrHCd907pcudMw11fYlT-JFgeEoz2erC7fdUo-UcOkUVwMwAufLnt9q6Nn_9z6BtG0Xlm</recordid><startdate>19990715</startdate><enddate>19990715</enddate><creator>Corey, E. 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source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
subjects | Benzhydryl Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Catalysis Guanidines - chemistry Hydrogen Cyanide - chemistry Imines - chemical synthesis Models, Molecular Nitriles - chemical synthesis Schiff Bases Stereoisomerism |
title | Enantioselective Synthesis of α-Amino Nitriles from N-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as Catalyst |
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