Multifunctional organoboron compounds for scalable natural product synthesis.

ABSTRACT: Efficient catalytic reactions that can generate C-C bonds enantioselectively, and ones that can produce trisubstituted alkenes diastereoselectively, are central to research in organic chemistry. Transformations that accomplish these two tasks simultaneously are in high demand, particularly if the catalysts, substrates and reagents are inexpensive and if the reaction conditions are mild. Here we report a facile multicomponent catalytic process that begins with a chemoselective, site-selective and diastereoselective copper-boron addition to a monosubstituted allene; the resulting boron-substituted organocopper intermediates then participate in a similarly selective allylic substitution. The products, which contain a stereogenic carbon centre, a monosubstituted alkene and an easily functional

SUBMITTER: Meng F 

PROVIDER: S-EPMC4267680 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature