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Highly Diastereoselective Preparation of Homoallylic Alcohols Containing Two Contiguous Quaternary Stereocenters in Acyclic Systems from Simple Terminal Alkynes

Bishnu Dutta, Noga Gilboa and Ilan Marek*

*The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000, Israel, Email: chilanmtx.technion.ac.il

B. Dutta, N. Gilboa, I. Marek, J. Am. Chem. Soc., 2010, 132, 5588-5589.

DOI: 10.1021/ja101371x (free Supporting Information)


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Abstract

A combined carbocupration of terminal alkynes followed by a zinc homologation and further reaction with ketones lead, in a single-pot operation, to homoallylic alcohols possessing two consecutive quaternary stereocenters with excellent diastereoselectivity.

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Key Words

homoallylic alcohols


ID: J48-Y2010-1120