Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones

被引：3

作者：

Raffier, Ludovic ^{[1
]}

Gutierrez, Osvaldo ^{[1
]}

Stanton, Gretchen R. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

Walsh, Patrick J. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANOMETALLICS | 2014年 / 33卷 / 19期

基金：

美国国家科学基金会;

关键词：

TUNABLE CINNAMATE LIGANDS; CARBONYL ADDITION; SPECTROSCOPIC CHARACTERIZATION; DIMETHYLALUMINUM CHLORIDE; STEREOSELECTIVE-SYNTHESIS; ALKOXY KETONES; PI-CHELATION; COORDINATION; COMPLEX; ALDEHYDES;

D O I：

10.1021/om5007006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to beta,gamma-unsaturated ketones. H-1 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 CC double bonds, broadening the 60 year old paradigm.

引用

页码：5371 / 5377

页数：7

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