Organocatalytic Michael Addition of Nitro Esters to α,β‐Unsaturated Aldehydes: Towards the Enantioselective Synthesis of  trans ‐3‐Substituted Proline Derivatives | Zendy

Han ManYi | Zendy; Zhang Yong | Zendy; Wang HuaiZhen | Zendy; An WanKai | Zendy; Ma BaoChun | Zendy; Zhang Yuan | Zendy; Wang Wei | Zendy

Premium

Organocatalytic Michael Addition of Nitro Esters to α,β‐Unsaturated Aldehydes: Towards the Enantioselective Synthesis of trans ‐3‐Substituted Proline Derivatives

Author(s) -

Han ManYi,

Zhang Yong,

Wang HuaiZhen,

An WanKai,

Ma BaoChun,

Zhang Yuan,

Wang Wei

Publication year - 2012

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201200538

Subject(s) - chemistry , enantioselective synthesis , michael reaction , organocatalysis , nitro , proline , silyl ether , adduct , organic chemistry , silylation , catalysis , amino acid , biochemistry , alkyl

A facile five‐step strategy has been developed for the enantioselective synthesis of trans ‐3‐substituted proline derivatives with high diasteroselectivity ( dr >20:1) and enantioselectivity (up to 97% ee ). The key step is the asymmetric organocatalytic Michael addition of nitro esters to α,β‐unsaturated aldehydes, which affords the chiral Michael adducts in high yields (up to 96%) and excellent enantioselectivity (up to 99% ee ) by using diarylprolinol silyl ether as the organocatalyst.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research