A New Method of Synthesizing Organic Molecules Showed Outstanding Chemical Reaction (IMAGE)

Tokyo University of Agriculture and Technology

A New Method of Synthesizing Organic Molecules Showed Outstanding Chemical Reaction

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We developed an efficient method for the diastereoselective synthesis of CF3-substituted spiroisochromans via C(sp3)¬-H bond functionalization involving sequential transformations ([1,5]-hydride shift/cyclization/elimination of MeOH/intramolecular Friedel-Crafts reaction). The salient feature of this reaction is that diastereoselectivity was affected by the subtle structural difference of the starting materials. This method gave the stereochemically defined CF3-substituted spiroisochromans, which is otherwise difficult to synthesize by the conventional method, and highlight the high synthetic potential of the internal redox reaction.

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FIGURE ADAPTED WITH PERMISSION FROM Org. Lett. 2019, 21, 2383?2387. COPYRIGHT © 2019 AMERICAN CHEMICAL SOCIETY

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