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

Seung Tae Kim; Rameshwar Prasad Pandit; Jaesook Yun; Do Hyun Ryu

doi:10.1021/acs.orglett.0c03937

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

Seung Tae Kim
, Rameshwar Prasad Pandit
, Jaesook Yun
, Do Hyun Ryu

Department of Chemistry

Sungkyunkwan University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	213-217
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.0c03937
State	Published - 1 Jan 2021

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abstract = "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.",

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AU - Pandit, Rameshwar Prasad

AU - Yun, Jaesook

AU - Ryu, Do Hyun

N1 - Publisher Copyright: ©

PY - 2021/1/1

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N2 - 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.

AB - 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.

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

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