One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds

Masaharu Sugiura; Yasuhiko Ashikari; Makoto Nakajima

doi:10.1021/acs.joc.5b01217

One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds

J Org Chem. 2015 Sep 4;80(17):8830-5. doi: 10.1021/acs.joc.5b01217. Epub 2015 Aug 26.

Authors

Masaharu Sugiura¹, Yasuhiko Ashikari¹, Makoto Nakajima¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kumamoto University , 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.

PMID: 26284292
DOI: 10.1021/acs.joc.5b01217

Abstract

TiCl4-promoted aldol reaction of ketones as aldol acceptors followed by elimination of the titanoxy group from the Ti-aldolates affords β,β-disubstituted α,β-unsaturated carbonyl compounds in a one-pot procedure. The use of additives, such as DMF, N,N,N',N'-tetramethylethylenediamine, and pyridine, in the elimination step was found to be important.

Publication types

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