Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst.

ABSTRACT: Catalytic systems that allow selective generation of any diastereomer of a reaction product bearing multiple stereocentres through minimal modification of a single catalyst scaffold remain elusive, particularly for carbon-carbon bond formations requiring simultaneous control of multiple selectivity factors. Here, we report a catalyst-directed pinpoint inversion of diastereochemical preference in the 1,6-addition of azlactones to δ-aryl dienyl carbonyl compounds with full control over other selectivities preserved. This rigorous diastereodivergence is enabled by the slight structural adjustment of a chiral iminophosphorane catalyst, providing access to all the stereoisomers with high regio-, distereo- and enantioselectivity. The utility of this method is demonstrated in the facile stereodiv

SUBMITTER: Uraguchi D 

PROVIDER: S-EPMC5364390 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature