The catalytic asymmetric halocyclization of alkene is a powerful and straightforward strategy for the synthesis of chiral heterocyclic compounds. Herein, an effective approach to chiral benzoxazine derivatives through organocatalyzed chlorocyclization of o-vinylanilides was reported. This method provides facile access to a series of chiral benzoxazines in good to excellent yields (up to 99% yield) and with high-level enantiocontrol (up to 92% ee).
The catalytic enantioselective desymmetrizing
bromoaminocyclization
of prochiral cyclohexa-1,4-dienes has been achieved by using chiral
anion phase-transfer catalysis, providing a range of enantioenriched cis-3a-arylhydroindoles bearing an all-carbon quaternary
stereocenter in good yields (up to 78%) and excellent enantioselectivities
(up to 97% ee). Furthermore, the potential application of this methodology
to natural product total synthesis was demonstrated by the asymmetric
synthesis of (+)-Mesembrane.
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