A homodinuclear Mn(III)2-Schiff base complex for catalytic asymmetric 1,4-additions of oxindoles to nitroalkenes

Yuko Kato; Makoto Furutachi; Zhihua Chen; Harunobu Mitsunuma; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1021/ja903566u

A homodinuclear Mn(III)2-Schiff base complex for catalytic asymmetric 1,4-additions of oxindoles to nitroalkenes

J Am Chem Soc. 2009 Jul 8;131(26):9168-9. doi: 10.1021/ja903566u.

Authors

Yuko Kato¹, Makoto Furutachi, Zhihua Chen, Harunobu Mitsunuma, Shigeki Matsunaga, Masakatsu Shibasaki

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 19522526
DOI: 10.1021/ja903566u

Abstract

Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to beta-aryl, beta-heteroaryl, and beta-alkenyl nitroalkenes are described. A new homodinuclear Mn(2)(OAc)(2)-Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn(2)(OAc)(2)-1 (1-5 mol %) promoted the 1,4-additions in 99-83% yield, 96-85% ee, and >30:1-5:1 dr at room temperature, providing useful chiral building blocks for the synthesis of beta-aminooxindoles with vicinal quaternary/tertiary carbon stereocenters.

Publication types

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

MeSH terms

Alkenes / chemistry*
Catalysis
Cyclization
Indoles / chemistry*
Molecular Structure
Nitro Compounds / chemistry*
Oxindoles
Schiff Bases / chemistry*
Stereoisomerism

Substances

Alkenes
Indoles
Nitro Compounds
Oxindoles
Schiff Bases
2-oxindole