Diastereoselective synthesis of psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-S(N)2' reaction

[reaction: see text] Acyclic psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy-beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforde...

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Bibliographic Details
Published in:Organic letters 2002-04, Vol.4 (7), p.1051-1054
Main Authors: Oishi, Shinya, Kamano, Takae, Niida, Ayumu, Odagaki, Yoshihiko, Tamamura, Hirokazu, Otaka, Akira, Hamanaka, Nobuyuki, Fujii, Nobutaka
Format: Article
Language:English
Subjects:
Alkylation
Copper
Dipeptides - chemical synthesis
Dipeptides - chemistry
Indicators and Reagents
Organometallic Compounds - chemistry
Stereoisomerism
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Summary:[reaction: see text] Acyclic psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy-beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the psi[(E)-CH=CMe]- or psi[(Z)-CH=CMe]-isomer, respectively, via anti-S(N)2' mechanism.
ISSN:1523-7060
DOI:10.1021/ol016834j