Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: metal-free, complementary anti- and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

Kazumasa Funabiki; Kei Matsunaga; Hiroshi Gonda; Hitoshi Yamamoto; Takao Arima; Yasuhiro Kubota; Masaki Matsui

doi:10.1021/jo101733j

Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: metal-free, complementary anti- and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

J Org Chem. 2011 Jan 7;76(1):285-8. doi: 10.1021/jo101733j. Epub 2010 Dec 3.

Authors

Kazumasa Funabiki¹, Kei Matsunaga, Hiroshi Gonda, Hitoshi Yamamoto, Takao Arima, Yasuhiro Kubota, Masaki Matsui

Affiliation

¹ Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. funabiki@gifu-u.ac.jp

PMID: 21126099
DOI: 10.1021/jo101733j

Abstract

A complete reversal of diastereoselectivity was observed for reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines, derived from propiophenones, that produce 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones. This process serves as the first reliable, metal-free, complementary anti- and syn-selective method to prepare 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones.

Publication types

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

MeSH terms

Acetaldehyde / analogs & derivatives*
Acetaldehyde / chemistry
Amines / chemistry*
Butanones / chemistry*
Catalysis
Imines / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Amines
Butanones
Imines
trifluoroacetaldehyde
Acetaldehyde