Diphenylprolinol Silyl Ether as a Catalyst in an Asymmetric, Catalytic, and Direct Michael Reaction of Nitroethanol with α,β-Unsaturated Aldehydes
Diphenylprolinol Silyl Ether as a Catalyst in an Asymmetric, Catalytic, and Direct Michael Reaction of Nitroethanol with α,β-Unsaturated Aldehydes
复制标题
DOI：
10.1021/ol901483x
复制
发表时间：
2009-09-17
期刊：
影响因子：
5.2
通讯作者：
Hayashi, Yujiro
中科院分区：
文献类型：
--
作者：
Gotoh, Hiroaki;Okamura, Daichi;Hayashi, Yujiro
二苯基脯氨醇硅醚是硝基乙醇与α，β-不饱和醛直接Michael反应的有效有机催化剂，异构化后得到1-羟基-反式-3，4-二取代四氢吡喃。生成的Michael加成产物是有用的合成中间体，其可以转化为具有季立构中心的手性四氢吡喃、3-取代的顺式和反式脯氨酸以及α-氨基酸衍生物。
Diphenylprolinol silyl ether was found to be an effective organocatalyst in the enantioselective and direct Michael reaction of nitroethanol and alpha,beta-unsaturated aldehydes, affording the 1-hydroxy-trans-3,4-disubstituted tetrahydropyrans after isomerization. The generated Michael addition products are useful synthetic Intermediates, which can be converted Into chiral tetrahydropyran with a quaternary stereocenter, 3-substituted cis- and trans-prolines, and alpha-amino acid derivatives.