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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 ?,?-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

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

Raffier Ludovic L Gutierrez Osvaldo O Stanton Gretchen R GR Kozlowski Marisa C MC Walsh Patrick J PJ

Organometallics 20140909 19

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. ...[more]

PMID: 25328269

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