Alkenes as Chelating Groups in Diastereoselective
Additions of Organometallics to Ketones
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Abstract
Alkenes have been discovered to be
chelating groups to Zn(II),
enforcing highly stereoselective additions of organozincs to β,γ-unsaturated
ketones. <sup>1</sup>H 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