Organic Chemistry Portal

Abstracts

Search:

Lithium Binaphtholate-Catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds

Shunsuke Kotani, Kenji Kukita, Kana Tanaka, Tomonori Ichibakase and Makoto Nakajima*

*Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan, Email: nakajimagpo.kumamoto-u.ac.jp

S. Kotani, K. Kukita, K. Tanaka, T. Ichibakase, M. Nakajima, J. Org. Chem., 2014, 79, 4817-4825.

DOI: 10.1021/jo5005394 (free Supporting Information)



see article for more reactions

Abstract

In an asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst, slow addition of the carbonyl compound improved the enantioselectivity. This reaction afforded diverse chiral secondary and tertiary propargylic alcohols in high yields and with good to high enantioselectivities.

see article for more examples



Key Words

propargyl alcohols


ID: J42-Y2014