American Chemical Society
ja8b13182_si_003.cif (597.84 kB)

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

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posted on 2019-01-28, 00:00 authored by Ye Wang, Wen-Yun Zhang, Shu-Li You
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.