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Highly Enantioselective Catalytic Alkynylation of Ketones – A Convenient Approach to Optically Active Propargylic Alcohols

✍ Scribed by Gui Lu; Xingshu Li; Yue-Ming Li; Fuk Yee Kwong; Albert S. C. Chan

Book ID
101422656
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
127 KB
Volume
348
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

The development of highly enantioselective catalysts involving Cu(OTf)~2~ and chiral camphorsulfonamides for the alkynylation of ketone is described. The influences of Lewis acids, reaction conditions and chiral ligands on the outcome of the reaction are discussed. The best enantioselectivity (up to 97 % ee) was obtained in the alkynylation of 2′‐chloroacetophenone. The scope of the reaction is also examined.

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✍ Robert A. Singer; Mary S. Shepard; Erick M. Carreira 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 393 KB

A catalytic, enantioselective ~i addition reaction of silyl ketene acetals with oq[i--ynals and 3 tool % of a chiral TiffV) complex is described. This process provides access to optically active ~-hydroxy-'l-alkynyl esters in 84-96% yields and 94-97% ee's.