H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.

ABSTRACT: The development of catalyst-controlled stereodivergent asymmetric catalysis is important for providing facile access to all stereoisomers of chiral products with multiple stereocenters from the same starting materials. Despite progress, new design strategies for diastereodivergent asymmetric catalysis are still highly desirable. Here we report the potency of H-bond donors as the governing factor to tune diastereoselectivity in a highly diastereoselective switchable enantioselective Michael addition of α-azido ketones to nitroolefins. While a newly developed bifunctional tertiary amine, phosphoramide, preferentially afforded syn-adducts, an analogous squaramide catalyst selectively gave anti-adducts. The resulting multifunctional tertiary azides can be converted to spiro-pyrro

SUBMITTER: Ding PG 

PROVIDER: S-EPMC8152593 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature