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Literature DB >> 15469267

Copper-catalyzed enantioselective conjugate addition of grignard reagents to acyclic enones.

Fernando López¹, Syuzanna R Harutyunyan, Adriaan J Minnaard, Ben L Feringa.

Abstract

A highly enantioselective Cu-catalyzed addition of Grignard reagents to acyclic aliphatic enones is described. In the presence of 5 mol % of CuBr.SMe2 and 6 mol % of JosiPhos diphosphine aliphatic enones react with Grignard reagents to provide beta-substituted linear ketones with high yields, regio-, and enantioselectivities.

Entities: Chemical

Year: 2004 PMID： 15469267 DOI： 10.1021/ja046632t

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

6 in total

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Authors: Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal: Science Date: 2013-03-29 Impact factor: 47.728

2. Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

Authors: Dingqiao Yang; Ping Hu; Yuhua Long; Yujuan Wu; Heping Zeng; Hui Wang; Xiongjun Zuo
Journal: Beilstein J Org Chem Date: 2009-10-09 Impact factor: 2.883

3. Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.

Authors: Michael D Clift; Regan J Thomson
Journal: J Am Chem Soc Date: 2009-10-14 Impact factor: 15.419

Copper-catalyzed enantioselective conjugate addition of grignard reagents to acyclic enones.

1. Photoredox activation for the direct β-arylation of ketones and aldehydes.

2. Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

3. Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.

4. Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis.

5. Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones.

6. Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach.