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Diastereoselective Ethynylation of Chiral α‐(Dibenzylamino) Aldehydes: Synthesis of meso ‐ and Homochiral C 2 ‐Symmetrical 1,6‐Diamino‐2,5‐diols
Author(s) -
Andrés José M.,
Pedrosa Rafael,
PérezEncabo Alfonso
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.200600214
Subject(s) - chemistry , enantiopure drug , diastereomer , bromide , stereochemistry , organic chemistry , enantioselective synthesis , medicinal chemistry , catalysis
Abstract Homochiral α‐(dibenzylamino) aldehydes, prepared from the corresponding α‐amino acids, react with ethynylmagnesium bromide in THF/Et 2 O at 0 °C to afford, in good yields and dr , propargylic 1,2‐amino alcohols; anti diastereomers were always formed as the major products in this reaction. These compounds are versatile intermediates in the synthesis of meso ‐ and enantiopure 1,6‐diamino‐2,5‐diols with C 2 symmetry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)