ArticleJournal of the American Chemical Society2011
Highly diastereoselective chelation-controlled additions to α-silyloxy ketones.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Chiral ruthenium complex/PhScience advances · 2025Article
- Genome-based discovery and total synthesis of janustatins, potent cytotoxins from a plant-associated bacterium.Nature chemistry · 2022Article
- Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.Chemical reviews · 2020Review
- A Highly Convergent Total Synthesis of Leustroducsin B.Journal of the American Chemical Society · 2015Article
- A useful methoxyvinyl cation equivalent: α-t-butyldimethylsilyl-α-methoxyacetaldehyde.Tetrahedron letters · 2015Article
- Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones.Organometallics · 2014Article
- Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.Organic letters · 2012Article
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Authors and funding
3 authors.
Funding
Abstract
The polar Felkin-Anh, Cornforth-Evans, and Cram-chelation models predict that the addition of organometallic reagents to silyl-protected α-hydroxy ketones proceeds via a nonchelation pathway to give anti-diol addition products. This prediction has held true for the vast majority of additions reported in the literature, and few methods for chelation-controlled additions of organometallic reagents to silyl-protected α-hydroxy ketones have been introduced. Herein, we present a general and highly diastereoselective method for the addition of dialkylzincs and (E)-di-, (E)-tri-, and (Z)-disubstituted vinylzinc reagents to α-silyloxy ketones using alkyl zinc halide Lewis acids, RZnX, to give chelation-controlled products (dr ≥18:1). The compatibility of organozinc reagents with other functional groups makes this method potentially very useful in complex molecule synthesis.
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