Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 47, Pages 20904-20908Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010234
Keywords
[2; 3]-rearrangement reactions; carbenes; chiral sulfides; sulfonium ylides; synergistic organocatalysis
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Funding
- National Natural Science Foundation of China [21825101]
- Hong Kong RGC [16300320]
- Shenzhen Science and Technology Innovation Commission [SGDX2019081623241924, JCYJ20170818085510474]
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The rearrangement of sulfur-containing aldehydes by using a sulfonium enamine intermediate as a formylcarbene mimetic is reported. This is an enantioselective, organocatalytic [2,3]-sigmatropic rearrangement enabling chiral cyclic sulfides bearing an alpha-quaternary chiral center to be prepared in high optical purity. The enantioselectivity is controlled with a cooperative organocatalyst pair consisting of a chiral amine and a chiral phosphoric acid (CPA). The synthetic versatility of this method is demonstrated by its rapid access to structurally diverse chiral spiro S-heterocycles.
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