Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 38, Pages 13492-13498Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907164
Keywords
diazo compounds; nickel; rearrangements; sulfur; ylides
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Funding
- National Natural Science Foundation of China [21625205]
- Graduate Student's Research and Innovation Foundation of Sichuan University [2018YJSY050]
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Catalytic enantioselective [2,3] Stevens and Sommelet-Hauser rearrangements of alpha-diazo pyrazoleamides with sulfides were achieved by utilizing chiral N,N '-dioxide/nickel((II)) complex catalysts. These rearrangements proceeded well under mild reaction conditions, providing rapid and facile access to a series of functionalized 1,6-dicarbonyls or sulfane-substituted phenylacetates with high to excellent enantioselectivities. The catalytic system shows excellent stereocontrol, discriminating between the heterotopic lone pairs of sulfur and controlling both the 1,3-proton transfer and the [2,3]-sigma rearrangement.
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