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Stereoselective Complete Reduction of α‐Alkyl‐β‐ketonitriles to anti γ‐Amino Alcohols
Author(s) -
De Nino Antonio,
Dalpozzo Renato,
Cupone Giovanna,
Maiuolo Loredana,
Procopio Antonio,
Tagarelli Antonio,
Bartoli Giuseppe
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:17<2924::aid-ejoc2924>3.0.co;2-5
Subject(s) - chemistry , borane , alkyl , stereoselectivity , dimethyl sulfide , cerium , lewis acids and bases , organic chemistry , sulfide , chloride , medicinal chemistry , catalysis , sulfur
The one‐pot reduction of α‐alkyl‐β‐ketonitriles to anti γ‐amino alcohols can be efficiently performed by borane/dimethyl sulfide complex in the presence of cerium chloride as Lewis acid. Selectivities are slightly worse than monoreduction but this drawback is overcome by much better yields. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)