Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 22, Pages 8471-8475Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001100
Keywords
asymmetric catalysis; organocatalysis; quaternary carbon centers; semipinacol rearrangement; tandem reactions
Categories
Funding
- NSFC [21502080, 21772071, 21871117, 21772076, 21702136, 91956203]
- 111 Program of MOE
- MOST [2018ZX09711001-005-002]
- STCSM [19JC1430100]
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An enantioselective aldehyde alpha-alkylation/semipinacol rearrangement was achieved through organo-SOMO catalysis. The catalytically generated enamine radical cation serves as a carbon radical electrophile that can stereoselectively add to the alkene of an allylic alcohol and initiate ensuing ring-expansion of cyclopropanol or cyclobutanol. This tandem reaction enables the production of a wide range of nonracemic functionalizable alpha-quaternary-delta-carbonyl cycloketones in high yields and excellent enantioselectivity from simple aldehydes and allylic alcohols. As a key step, the intramolecular reaction was also successfully applied in the asymmetric total synthesis of (+)-cerapicol.
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