Kinetic Resolution of Sulfinamides via Asymmetric N‑Allylic Alkylation

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita–Baylis–Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition,...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 21; pp. 8499 - 8504
Main Authors Zheng, Gao-Liang, Lu, Chenxi, Cheng, Jin-Pei, Li, Xin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
SULFOXIDES
CHIRAL SULFINAMIDES
LIGANDS
ACIDS
UMPOLUNG ADDITION
PHOSPHINE OXIDES
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Summary:An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita–Baylis–Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03221