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Pd(0)-Catalyzed Intramolecular Reductive Heck Reaction of Vinyl Iodide and Oxime Ether: Enantioselective Synthesis of Cyclic Allylic N -Alkoxy Amine.

Authors :
Yang N
Dong M
Tong X
Source :
Organic letters [Org Lett] 2022 Apr 01; Vol. 24 (12), pp. 2457-2461. Date of Electronic Publication: 2022 Mar 23.
Publication Year :
2022

Abstract

Whereas the intramolecular reductive Heck reaction of aryl/vinyl halide and alkene has been well documented, the oxime analogue remains extremely elusive. Herein we report the Pd(0)-catalyzed intramolecular reductive Heck reaction of vinyl iodide and oxime ether with the use of formic acid as the reductant. It is found that the TsOH additive plays a crucial role in the reaction efficiency, and the ( S )-SEGPhos ligand enables cyclic allylic N -alkoxy amine products with high enantioselectivity.

Details

Language :
English
ISSN :
1523-7052
Volume :
24
Issue :
12
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
35319217
Full Text :
https://doi.org/10.1021/acs.orglett.2c00823