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The Proline‐Catalyzed Asymmetric Amination of Branched Aldehydes
Author(s) -
Baumann Thomas,
Vogt Henning,
Bräse Stefan
Publication year - 2007
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/ejoc.200600654
Subject(s) - chemistry , hydrazide , amination , yield (engineering) , reductive amination , organic chemistry , catalysis , proline , alkylation , amino acid , bond cleavage , residue (chemistry) , derivative (finance) , cleavage (geology) , aldol reaction , combinatorial chemistry , biochemistry , materials science , geotechnical engineering , fracture (geology) , economics , financial economics , engineering , metallurgy
An efficient access to configurationally stable α,α‐disubstituted α‐amino aldehydes, oxazolidinones, and α‐amino acids has been presented. Starting from simple and easily available racemic aldehydes, the α‐aminated products were obtained using azodicarboxylates as the nitrogen source in up to 86 % ee and moderate to excellent yield. These products could further be converted both into the corresponding α‐amino alcohols and, depending on the residue of the azodicarboxylates and the reaction conditions, into the oxazolidinones. On the other hand, oxidation towards the carboxylic acid and cleavage of the hydrazide bond under mild conditions revealed the free α‐alkylated phenylglycine derivative. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)