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

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A nickel(0) N-heterocyclic carbene complex effectively catalyzes the diastereoselective coupling of alpha-silyloxy aldehydes and alkynylsilanes to produce anti-1,2-diols with excellent scope and diastereoselection. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

Kanicha Sa‐ei; John Montgomery

doi:10.1021/ol061579u

August 29, 2006Organic LettersOpen Access

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

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Abstract

The catalytic, diastereoselective coupling of alpha-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excellent across a range of substrates.

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Sa‐ei et al. (2006) studied this question.

synapsesocial.com/papers/6a08d96e720b08f65a5b6fd8 https://doi.org/10.1021/ol061579u

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

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

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Abstract

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