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Ketones and Aldehydes as O-Nucleophiles in Iridium-Catalyzed Intramolecular Asymmetric Allylic Substitution Reaction

Author:
Wang, Ye, Zhang, Wen-Yun, You, Shu-Li
Source:
Journal of the American Chemical Society 2019 v.141 no.6 pp. 2228-2232
ISSN:
1520-5126
Subject:
aldehydes, enantioselective synthesis, enols, iridium, ketones
Abstract:
Ketones and aldehydes are employed as enol O-nucleophiles in an iridium-catalyzed asymmetric allylic substitution reaction. The reaction proceeds well in the presence of a well-defined chiral iridium complex under mild conditions. A series of chiral 2H-1,4-oxazine skeletons can be obtained in up to 94% yield with 99% ee. The utility of this novel method has been demonstrated by its implementation in the first enantioselective synthesis of (+)-chelonin A.
Agid:
6308335