Enantioselective alkynylation of ketones with trimethoxysilylalkynes using lithium binaphtholate as a catalyst

✍ Scribed by Kana Tanaka; Tomohiro Ueda; Tomonori Ichibakase; Makoto Nakajima

• Book ID: 104097511
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 171 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.02.084

✦ Synopsis

Chiral lithium 3,3 0 -diphenylbinaphtholate successfully catalyzed the alkynylation of ketone with trimethoxysilylalkyne, affording chiral tertiary propargylic alcohols in high chemical yields and high enantioselectivities. The present reaction could be extended to the alkynylation of acetylpyridine, which afforded a biologically active pyridyl propargylic alcohol in good enantioselectivity.