控制铜氢化物还原 Morita-Baylis-Hillman 加合物的化学选择性、区域选择性和对映选择性。
Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts.
机构信息
Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
出版信息
Org Lett. 2017 Jan 20;19(2):328-331. doi: 10.1021/acs.orglett.6b03464. Epub 2017 Jan 11.
Nonracemically ligated copper hydride can be used to effect tandem S2'/1,2-reductions of racemic Morita-Baylis-Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined enoates by taking advantage of a bulky, oligomeric, in situ generated trialkoxysiloxane leaving group. Finally, an atypical conversion of easily arrived at MBH alcohol derivatives to nonracemic allylic alcohols is disclosed.
非对映选择性键合的铜氢化物可用于对映体 Morita-Baylis-Hillman（MBH）乙酸酯进行串联 S2'/1,2-还原，以获得具有确定烯烃几何形状的手性烯丙基醇。MBH 酯，包括具有β取代基的酯，可以通过利用体积庞大的、齐聚的、原位生成的三烷氧基硅烷离去基团转化为立体定义的烯酸酯。最后，揭示了一种将易于获得的 MBH 醇衍生物转化为非对映体烯丙基醇的非典型转化。
Zotero 插件