对映体富集的双官能型烯丙基硅烷在不对称合成邻位保护的 2-甲基-1,3-二醇中的应用。

Enantioenriched bifunctional crotylsilanes for the asymmetric synthesis of orthogonally protected 2-methyl-1,3-diols.

机构信息

Department of Chemistry, University of Texas at San Antonio , San Antonio, Texas 78249, United States.

出版信息

Org Lett. 2013 Oct 4;15(19):5142-5. doi: 10.1021/ol4026167. Epub 2013 Sep 24.

Abstract

Enantiomerically pure α-substituted crotylsilane reagents I and ent-I undergo asymmetric aldehyde crotylation followed by Ir(I)-catalyzed diastereoselective allylic etherification to give a variety of orthogonally protected 2-methyl-1,3-diols at the synthetically useful level of yields and stereoselectivity. The reagents are air-stable and bifunctional so that they can be used in these reactions sequentially without recourse to functional group adjustments.

摘要

对映体纯的 α-取代的烯丙基硅烷试剂 I 和 ent-I 经历不对称醛烯丙基化反应，然后进行 Ir(I)-催化的非对映选择性烯丙基醚化反应，以在合成上有用的产率和立体选择性得到各种正交保护的 2-甲基-1,3-二醇。这些试剂是空气稳定的和双功能的，因此它们可以在这些反应中顺序使用，而无需诉诸官能团调整。