Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted Allenylboronates

Hajime Ito*, Yusuke Sasaki and Masaya Sawamura*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email: sawamurasci.hokudai.ac.jp, hajitosci.hokudai.ac.jp

H. Ito, Y. Sasaki, M. Sawamura, J. Am. Chem. Soc., 2008, 130, 15774-15775.

DOI: 10.1021/ja806602h

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Abstract

A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboronates with different substitution patterns, those with functional groups, and an axially chiral one. A Lewis acid promoted stereoselective addition of allenylboronates to aldehydes leads to homopropargylic alcohols.

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Key Words

Allenes, Boronates

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ID: J48-Y2008-3480