Pd(II)/Pd(IV) catalytic enantioselective synthesis of bicyclo[3.1.0]hexanes via oxidative cyclization of enynes

Tetsuya Tsujihara; Kazuhiro Takenaka; Kiyotaka Onitsuka; Minoru Hatanaka; Hiroaki Sasai

doi:10.1021/ja809965e

Pd(II)/Pd(IV) catalytic enantioselective synthesis of bicyclo[3.1.0]hexanes via oxidative cyclization of enynes

J Am Chem Soc. 2009 Mar 18;131(10):3452-3. doi: 10.1021/ja809965e.

Authors

Tetsuya Tsujihara¹, Kazuhiro Takenaka, Kiyotaka Onitsuka, Minoru Hatanaka, Hiroaki Sasai

Affiliation

¹ Department of Medicinal Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan.

PMID: 19275254
DOI: 10.1021/ja809965e

Abstract

The first asymmetric Pd(II)/Pd(IV) catalysis has been achieved by employing the combination of a hypervalent iodine reagent and a chiral ligand, SPRIX. Enantioselective cyclization of enyne derivatives catalyzed by the Pd-i-Pr-SPRIX complex furnished lactones bearing a bicyclo[3.1.0]hexane skeleton with up to 95% ee.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Catalysis
Cyclization
Oxidation-Reduction
Palladium / chemistry*
Stereoisomerism

Substances

Bridged Bicyclo Compounds
bicyclo(3.1.0)hexane
Palladium