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Prolinethiol ether catalysis in an asymmetric Michael reaction: solvent-free synthesis of functionalized monohaloalkenes.

The Journal of organic chemistry (2013-01-05)
Ai-Bao Xia, Chao Wu, Dan-Qian Xu, Yi-Feng Wang, Xiao-Hua Du, Zhao-Bo Li, Zhen-Yuan Xu
ABSTRACT

The organocatalytic Michael reaction of ketones with γ-monohalonitrodienes catalyzed by chiral prolinethiol ether under solvent-free conditions was developed. The described method represents a novel approach for accessing highly functionalized monohaloalkenes with α, β-stereocenters of up to >99% ee.

MATERIALS
Product Number
Brand
Product Description

Supelco
Diethyl ether, analytical standard
Sigma-Aldrich
Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%
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Diethyl ether, reagent grade, ≥98%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor
Sigma-Aldrich
Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor
Supelco
Ethyl ether solution, certified reference material, 2000 μg/mL in methanol