Asymmetric synthesis of bicyclo[n.1.0]alkanes by the enantioselective 1,3-CH insertion reaction of chiral magnesium carbenoids

被引：13

作者：

Satoh, Tsuyoshi ^{[1
]}

Kuramoto, Takayuki ^{[1
]}

Ogata, Shingo ^{[1
]}

Watanabe, Hiroyuki ^{[1
]}

Saitou, Takahito ^{[1
]}

Tadokoro, Makoto ^{[1
]}

机构：

[1] Tokyo Univ Sci, Grad Sch Chem Sci & Technol, Shinjuku Ku, Tokyo 1620826, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 01期

关键词：

AMINO-ACID DERIVATIVES; C-H ACTIVATION; GRIGNARD-REAGENTS; ORGANIC-SYNTHESIS; CYCLIC-KETONES; SULFOXIDES; CHEMISTRY; MECHANISM;

D O I：

10.1016/j.tetasy.2009.12.027

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of enantiomerically pure 1-chlorovinyl p-tolyl sulfoxides, derived from cyclic ketones and (R)-chloromethyl p-tolyl sulfoxide, with the lithium enolate of tert-butyl carboxylates gave adducts in quantitative yields as single diastereomers The adducts were treated with i-PrMgCl in toluene to afford optically active bicyclo[n 1 0]alkanes bearing a tert-butyl carboxylate moiety in up to 99% enantiomeric excess through the enantioselective 1,3-CH insertion reaction of the generated chiral magnesium carbenoids. This is the first example of the enantioselective 1,3-CH insertion reaction of magnesium carbenoid (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1 / 5

页数：5

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