Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones | Zendy

Ludovic Raffier | Zendy; Osvaldo Gutiérrez | Zendy; Gretchen R. Stanton | Zendy; Marisa C. Kozlowski | Zendy; Patrick J. Walsh | Zendy

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Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones

Author(s) -

Ludovic Raffier,

Osvaldo Gutiérrez,

Gretchen R. Stanton,

Marisa C. Kozlowski,

Patrick J. Walsh

Publication year - 2014

Publication title -

organometallics

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.231

H-Index - 172

eISSN - 1520-6041

pISSN - 0276-7333

DOI - 10.1021/om5007006

Subject(s) - chemistry , chelation , heteroatom , lewis acids and bases , stereoselectivity , addition reaction , organic chemistry , medicinal chemistry , stereochemistry , ring (chemistry) , catalysis

Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to β,γ-unsaturated ketones. 1 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.

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