Highly Diastereoselective Preparation of anti-1,2-Diols by Catalytic Addition of Alkynylsilanes to α-Silyloxyaldehydes

Kanicha Sa-ei and John Montgomery*

*Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA, Email: jmontgumich.edu

K. Sa-ei, J. Montgomery, Org. Lett., 2006, 8, 4441-4443.

DOI: 10.1021/ol061579u

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Abstract

A nickel(0) N-heterocyclic carbene complex-catalyzed coupling of α-silyloxy aldehydes and alkynylsilanes provides an effective entry to various anti-1,2-diols with excellent diastereoselectivity.

see article for more examples

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Ligand-Dependent Scope and Divergent Mechanistic Behavior in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes

G. M. Mahandru, G. Liu, J. Montgomery, J. Am. Chem. Soc., 2004, 126, 3698-3699.

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Key Words

Diols, Allylic Alcohols, Silanes, Multicomponent Reactions

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ID: J54-Y2006-2950