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

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

676845

Sigma-Aldrich

Diethyl ether, ACS reagent, ≥98.0%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor

673811

Sigma-Aldrich

Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor

32203

Sigma-Aldrich

Diethyl ether, contains BHT as inhibitor, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

309966

Sigma-Aldrich

Diethyl ether, suitable for HPLC, ≥99.9%, inhibitor-free

346136

Sigma-Aldrich

Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor

09-1832

Sigma-Aldrich

Diethyl ether, JIS 1000, suitable for residue analysis, ≥99.5%

09-1833

Sigma-Aldrich

Diethyl ether, suitable for residue analysis, JIS 5000

09-1800

Sigma-Aldrich

Diethyl ether, JIS special grade, ≥99.5%

09-1810

Sigma-Aldrich

Diethyl ether, SAJ first grade, ≥99.0%

09-1830

Sigma-Aldrich

Diethyl ether, JIS 300, ≥99.5%, suitable for residue analysis

09-1812

Sigma-Aldrich

Diethyl ether, ≥99.5%

24004

Sigma-Aldrich

Diethyl ether, puriss., contains ~5 mg/L 2,6-di-tert.-butyl-4-methylphenol as stabilizer, meets analytical specification of Ph. Eur., BP, ≥99.5% (GC)

91238

Supelco

Diethyl ether, analytical standard

296082

Sigma-Aldrich

Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%

346144

Sigma-Aldrich

Diethyl ether, reagent grade, ≥98%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor