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Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of Racemic Intermediates from Anchimeric Oxygen Borrowing.

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We report a chiral phosphoric acid catalyzed bromocyclization/regiodivergent reaction of racemic intermediates sequence, which is enabled by anchimeric oxygen borrowing. Different types of alkenes are applicable, and both enantiomers of… Click to show full abstract

We report a chiral phosphoric acid catalyzed bromocyclization/regiodivergent reaction of racemic intermediates sequence, which is enabled by anchimeric oxygen borrowing. Different types of alkenes are applicable, and both enantiomers of the bromohydrin products were obtained in generally excellent yields and enantioselectivities. In addition, an example of enantioconvergent synthesis from the two isomeric products is presented.

Keywords: racemic intermediates; synthesis enantioenriched; oxygen borrowing; anchimeric oxygen

Journal Title: Journal of the American Chemical Society
Year Published: 2018

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