Stereloselective aldol-type cyclization reaction mediated by dibutylboron triflate/diisopropylethylamine

被引:19
作者
Das, S
Li, LS
Sinha, SC
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ol036229b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dibutylboron triflate/diisopropylethylamine mediated aldol-type cyclization provides an expedient route for the stereoselective synthesis of cyclic ethers in a single step. The method is highly efficient for the stereoselective synthesis of 4-cis-tetrahydropyranones. The reaction is proposed to proceed via an S(N)1-type mechanism through a chair-like transition state, in which both substituents occupy equatorial positions.
引用
收藏
页码:123 / 126
页数:4
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