Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 7, Pages 1913-1917Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711813
Keywords
cycloaddition; halogens; enolates; organocatalysis; spirocompounds
Categories
Funding
- NSFC [21502009, 21702021]
- Science & Technology Department of Sichuan Province [2017JQ0032]
- Thousand Talents Program of Sichuan Province
- Chengdu Talents Program
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Asymmetric construction of halogenated quaternary carbon centers under mild reaction conditions remains challenging. Reported here is an unprecedented and highly stereoselective Bronsted base catalyzed [4+2] cycloaddition between either alpha-chloro-or alpha-bromoaldehydes and cyclic enones. The key intermediate, an alpha-halogenated enolate, is susceptible to dehalogenation and can be stabilized and stereochemically controlled using bifunctional tertiary amines. This method provides facile access to a collection of optically pure bicyclic dihydropyrans having three contiguous stereocenters, including a halogen-bearing quaternary carbon center. Of note, the product can be transformed in situ into densely functionalized spirocyclopropanes in a highly efficient and stereoselective manner.
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