Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones.

ABSTRACT: Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to β,γ-unsaturated ketones. ¹H NMR studies and DFT calculations provide support for this surprising chelation mode. The results expand the range of coordinating groups for chelation-controlled carbonyl additions from heteroatom Lewis bases to simple C-C double bonds, broadening the 60 year old paradigm.

SUBMITTER: Raffier L 

PROVIDER: S-EPMC4195513 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature