Enantioselective Mukaiyama-Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(II)-complexes at ambient temperature

被引：16

作者：

Rout, Subhrajit ^{[1
]}

Ray, Sumit K. ^{[2
]}

Singh, Vinod K. ^{[1
,2
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 460023, MP, India

[2] Indian Inst Technol, Dept Chem, Kanpur 208016, UP, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 27期

关键词：

SILYL ENOL ETHERS; DIELS-ALDER; ALLYLIC OXIDATION; SILYLKETENE ACETALS; ADDITION-REACTION; COPPER-COMPLEXES; ACYCLIC ENONES; EFFICIENT; OLEFINS; DERIVATIVES;

D O I：

10.1039/c3ob40445e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral PYBOX-DIPH-Zn(II) catalyzed enantioselective Mukaiyama-Michael reaction of acyclic Ad enol ethers with 2-enoylpyridine N-oxides has been studied in external additive free conditions at ambient temperature. The methodology offers straightforward access to a variety of functionalized chiral 1,5-dicarbonyl compounds, which could easily be elaborated into synthetically viable pyrones via hydrolysis followed by cyclization. A transition state model has been proposed to explain the stereochemical outcome.

引用

页码：4537 / 4545

页数：9

共 4 条

[1] Enantioselective Synthesis of Coumarin Derivatives by PYBOX-DIPH-Zn(II) Complex Catalyzed Michael Reaction
Ray, Sumit K.
Singh, Pradeep K.
Molleti, Nagaraju
Singh, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) : 8802 - 8808
[2] Enantioselective Friedel-Crafts Alkylation of Pyrroles Catalyzed by PYBOX-DIPH-Zn(II) Complexes
Singh, Pradeep K.
Singh, Vinod K.
ORGANIC LETTERS, 2010, 12 (01) : 80 - 83
[3] Highly Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes
Li, Lijun
Zhang, Sheng
Hu, Yanbin
Li, Yanan
Li, Chong
Zha, Zhenggen
Wang, Zhiyong
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) : 12885 - 12888
[4] Copper(II)-catalyzed enantioselective conjugate addition of nitro esters to 2-enoyl-pyridine N-oxides
Sun, Jianan
Li, Yanan
Gui, Yang
Xu, Youguo
Zha, Zhenggen
Wang, Zhiyong
CHINESE CHEMICAL LETTERS, 2019, 30 (03) : 569 - 572

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