Enantioselective Cyclopropanation/[1,5]-Hydrogen Shift to Access Rauhut–Currier Product

A Michael addition initiated cyclopropanation/[1,5]-hydrogen shift has been developed for the enantioselective synthesis of Rauhut–Currier products. The reaction of α-alkyl diazoesters and in situ generated o-quinone methides proceeds in the presence of chiral oxazaborolidinium ion, providing Z-ster...

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Bibliographic Details
Published in:Organic letters 2021-01, Vol.23 (1), p.213-217
Main Authors: Kim, Seung Tae, Pandit, Rameshwar Prasad, Yun, Jaesook, Ryu, Do Hyun
Format: Article
Language:English
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Summary:A Michael addition initiated cyclopropanation/[1,5]-hydrogen shift has been developed for the enantioselective synthesis of Rauhut–Currier products. The reaction of α-alkyl diazoesters and in situ generated o-quinone methides proceeds in the presence of chiral oxazaborolidinium ion, providing Z-stereocontrolled Rauhut–Currier products in high yields (up to 96%) with excellent Z/E selectivities (>20:1) and enantioselectivities (up to >99% ee). The synthetic utility was illustrated by conversion of the product to 3,4-dihydrocoumarins with two adjacent chiral stereocenters.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03937