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Straightforward Synthesis of Chiral Silylated Amino Acids through Hydrosilylation
Author(s) -
Marchand Damien,
Martinez Jean,
Cavelier Florine
Publication year - 2008
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.200800066
Subject(s) - hydrosilylation , chemistry , silane , amino acid , reagent , catalysis , organic chemistry , silicon , peptide synthesis , combinatorial chemistry , biochemistry
A method using hydrosilylation of unsaturated amino acids was developed and optimised to obtain silylated amino acids. The platinum (Bu 4 N) 2 PtCl 6 complex was identified as the best catalyst, and the procedure tolerated different unsaturated substrates, silane reagents and protecting groups. Seven silicon‐containing α‐amino acids were prepared in an enantiomerically pure form under mild conditions in good yields with orthogonal protections for versatile use in peptide synthesis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)