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Highly Selective Synthesis of ( E )‐Alkene Isosteric Dipeptides With High Optical Purity via RCu(CN)Li·BF 3 Mediated Reaction
Author(s) -
Ibuka Toshiro,
Habashita Hiromu,
Funakoshi Susumu,
Fujii Nobutaka,
Oguchi Yusaku,
Uyehara Tadao,
Yamamoto Yoshinori
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199008011
Subject(s) - stereocenter , alkene , chemistry , yield (engineering) , dipeptide , reagent , stereochemistry , chirality (physics) , enantioselective synthesis , double bond , medicinal chemistry , peptide , organic chemistry , catalysis , biochemistry , materials science , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , metallurgy
The configuration of the double bond in β,γ position and of the stereogenic α‐carbon atom of E alkenes 2 , isosteric to dipeptides, may be controlled via 1,3‐chirality transfer from γ‐mesyloxy(MsO)‐α,β‐enoates 1 . Methyl, isobutyl, and benzyl cuprates serve as reagents and, in almost every case, the yield is over 90% and the diastereoselectivity over 95:5. Alkenes isosteric to dipeptides are of interest as enzymatically nonhydrolyzable peptide building blocks.