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

Y.-M. Cao, D. Lentz, M. Christmann

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.

Title
65. Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of Racemic Intermediates from Anchimeric Oxygen Borrowing
Author
Y.-M. Cao, D. Lentz, M. Christmann
Identifier
DOI: 10.1021/jacs.8b06432
Citation
J. Am. Chem. Soc. 2018, 140, 10677–10681.