Engineering Catalysts for Enantioselective Addition of Diethylzinc to Aldehydes with Racemic Amino Alcohols: Nonlinear Effects in Asymmetric Deactivation of Racemic Catalysts

Jiang Long; Kuiling Ding

doi:10.1002/1521-3773(20010202)40:3<544::AID-ANIE544>3.0.CO;2-8

Engineering Catalysts for Enantioselective Addition of Diethylzinc to Aldehydes with Racemic Amino Alcohols: Nonlinear Effects in Asymmetric Deactivation of Racemic Catalysts

Angew Chem Int Ed Engl. 2001 Feb 2;40(3):544-547. doi: 10.1002/1521-3773(20010202)40:3<544::AID-ANIE544>3.0.CO;2-8.

Authors

Jiang Long¹, Kuiling Ding¹

Affiliation

¹ Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 354 Fenglin Road, Shanghai 200032, China, Fax: (+86) 21-6416-6128.

PMID: 29712026
DOI: 10.1002/1521-3773(20010202)40:3<544::AID-ANIE544>3.0.CO;2-8

Abstract

Correct additions make a difference: Asymmetric deactivation and asymmetric amplification concepts coupled with a high-throughput screening technique provided a successful strategy for designing a highly enantioselective catalytic system by simple combination of a racemic amino alcohol (rac-DB) and a nonracemic additive (AA). The example in the scheme shows the conversion of 1 into 2 with up to 92.7 % ee.

Keywords: asymmetric catalysis; asymmetric deactivation; high-throughput screening; nonlinear effects; zinc.