Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids

Shuichi Nakamura; Masashi Hayashi; Yuichi Hiramatsu; Norio Shibata; Yasuhiro Funahashi; Takeshi Toru

doi:10.1021/ja908940e

Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids

J Am Chem Soc. 2009 Dec 30;131(51):18240-1. doi: 10.1021/ja908940e.

Authors

Shuichi Nakamura¹, Masashi Hayashi, Yuichi Hiramatsu, Norio Shibata, Yasuhiro Funahashi, Takeshi Toru

Affiliation

¹ Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp

PMID: 19958032
DOI: 10.1021/ja908940e

Abstract

Organocatalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids and Na(2)CO(3) afforded products with high enantioselectivity. Both enantiomers of alpha-amino phosphonates can be prepared by using pseudoenantiomeric cinchona alkaloids. The catalyst loading of cinchona alkaloids can be reduced to 0.5 mol % without a significant loss of enantioselectivity.

Publication types

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

MeSH terms

Catalysis
Cinchona Alkaloids / chemistry*
Imines / chemistry*
Nitriles / chemistry*
Organophosphonates / chemistry*
Stereoisomerism

Substances

Cinchona Alkaloids
Imines
Nitriles
Organophosphonates
ketimine