4.8 Article

Facial Selectivity and Stereospecificity in the (4+3) Cycloaddition of Epoxy Enol Silanes

Journal

ORGANIC LETTERS
Volume 13, Issue 5, Pages 864-867

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102897d

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Funding

  1. University of Hong Kong Strategic Research Theme on Drugs
  2. Council of Hong Kong SAR [GRF HKU 7017/06P, 7015/10P]

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The scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial selectivity and stereospecificity for the stereochemistry of the epoxy enol silane.

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