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Towards the Synthesis of Highly Functionalized Chiral α‐Amino Nitriles by Aminative Cyanation and Their Synthetic Applications
Author(s) -
Bernardi Luca,
Bonini Bianca F.,
Capitò Elena,
ComesFranchini Mauro,
Dessole Gabriella,
Fini Francesco,
Fochi Mariafrancesca,
Herrera Raquel P.,
Ricci Alfredo
Publication year - 2006
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.200500501
Subject(s) - cyanation , chemistry , borane , combinatorial chemistry , catalysis , amino acid , organic chemistry , enantioselective synthesis , nitrile , stereochemistry , biochemistry
Abstract The cyanobis(dibenzylamino)borane‐mediated transformation of chiral aldehydes into the corresponding α‐amino nitriles is described. Starting from these compounds short synthetic routes can be envisaged for obtaining diastereomerically pure functionalized 1,2‐diamines and hydroxylated α‐amino acids that are of interest as core key units of biologically active substances or as potential ligands for asymmetric catalysis. The stereochemical outcome of the aminative cyanation reaction is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)