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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.