Diastereoselective and Enantioselective Formal [4+1] Ylide Annulation Leading to Optically Active Isoxazoline N‐Oxides

A diastereoselective and enantioselective formal [4+1] ylide annulation of chiral sulfonium salts with various substituted α‐substituted nitroalkene leading to optically active isoxazoline N‐oxides using CF3SO3− as a key anion has been explored. The salient features of this methodology include high...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-03, Vol.364 (6), p.1185-1199
Main Authors: Gong, Pin, Wang, Jing, Yao, Wen‐Bo, Xie, Xuan‐Sheng, Xie, Jian‐Wu
Format: Article
Language:English
Subjects:
[4+1] Annulations
Asymmetric Reactions
Chemical reactions
Enantiomers
Isoxazoline N-oxides
Nitroalkenes
Optical activity
Organic chemistry
Oxides
Stereoselectivity
Substitutes
Substrates
Sulfonium salts
Sulfur Ylides
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Summary:A diastereoselective and enantioselective formal [4+1] ylide annulation of chiral sulfonium salts with various substituted α‐substituted nitroalkene leading to optically active isoxazoline N‐oxides using CF3SO3− as a key anion has been explored. The salient features of this methodology include high diastereo‐ and enantioselecties, easily available starting materials, mild reaction conditions, simple procedure, broad substrate scope and the isoxazoline N‐oxides are conveniently transformed into other functionalized compounds.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101474