Diastereoselective prins-type reaction of cycloalkenylcyclopropanol silyl ethers and α,β-unsaturated aldehyde acetals

被引：22

作者：

Lysenko, Ivan L. ^{[1
]}

Oh, Heong-Sub ^{[1
]}

Cha, Jin Kun ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 21期

关键词：

D O I：

10.1021/jo071272o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic addition of 1-(1-cyclohexenyl)-1-cyclopropanol trimethylsilyl ether to a,P-unsaturated aldehyde acetals under Lewis acidic conditions proceeds with good to excellent diastereoselectivity to afford spirocyclobutanones containing three contiguous stereocenters. A convenient entry to enantioselective syntheses is available by use of a nonracemic C-2-symmetric acetal. Elaboration of the resulting adducts provides ready access to medium-sized carbocycles.

引用

页码：7903 / 7908

页数：6

共 54 条

[51] USE OF CYCLOPROPANES AND THEIR DERIVATIVES IN ORGANIC-SYNTHESIS [J].