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  • Copper-catalyzed asymmetric conjugate addition of diethylzinc to alpha,beta-unsaturated imines derived from alpha-aminoacids. Enantioselective synthesis of gamma-substituted alpha-dehydroaminoesters.

Copper-catalyzed asymmetric conjugate addition of diethylzinc to alpha,beta-unsaturated imines derived from alpha-aminoacids. Enantioselective synthesis of gamma-substituted alpha-dehydroaminoesters.

Organic letters (2006-11-03)
Francisco Palacios, Javier Vicario
ABSTRACT

[Structure: see text] A highly enantioselective synthesis of alpha-dehydroaminoacids with a stereogenic center in the gamma position through copper-catalyzed asymmetric conjugate addition of diethylzinc to alpha,beta-unsaturated imines using a TADDOL-derived phosphoramidite complex is reported.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(3aR,8aR)-(−)-(2,2-Dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine, 96%
Sigma-Aldrich
Diethylzinc solution, 15 wt. % in toluene
Sigma-Aldrich
Diethylzinc, ≥52 wt. % Zn basis
Sigma-Aldrich
Diethylzinc solution, 1.0 M in hexanes
Sigma-Aldrich
Diethylzinc solution, 1.0 M in heptane