Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 36, Pages 12491-12496Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907115
Keywords
dual catalysis; quaternary centers; semipinacol rearrangement; spirocycles; sulfur compounds
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Funding
- National Natural Science Foundation of China-Yunnan Joint Fund [21702135, 21642004, 21290181, 21672145, 21871117, 21871178] Funding Source: Medline
- The Drug Innovation Major Project of the Ministry of Science and Technology of China [2018ZX09711001-005-002] Funding Source: Medline
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An enantioselective sulfenylation/semipinacol rearrangement of 1,1-disubstituted and trisubstituted allylic alcohols was accomplished with a chiral Lewis base and a chiral Bronsted acid as cocatalysts, generating various beta-arylthio ketones bearing an all-carbon quaternary center in moderate to excellent yields and excellent enantioselectivities. These chiral arylthio ketone products are common intermediates with many applications, for example, in the design of new chiral catalysts/ligands and the total synthesis of natural products. Computational studies (DFT calculations) were carried out to explain the enantioselectivity and the role of the chiral Bronsted acid. Additionally, the synthetic utility of this method was exemplified by an enantioselective total synthesis of (-)-herbertene and a one-pot synthesis of a chiral sulfoxide and sulfone.
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