Chiral Bicyclic Guanidine-Catalysed Conjugate Addition of α-Fluoro-β-Ketoesters to Cyclic Enones-Reference-Cited by-同舟云学术

Chiral Bicyclic Guanidine-Catalysed Conjugate Addition of α-Fluoro-β-Ketoesters to Cyclic Enones

Published:2014 Issue:7 Volume:67 Page:1119
ISSN:0004-9425
Container-title:Australian Journal of Chemistry
language:en
Short-container-title:Aust. J. Chem.

Author:

Jing Zhenzhong,Liu Jin,Chin Kek Foo,Chen Wenchao,Tan Choon-Hong,Jiang Zhiyong

Abstract

By utilising a chiral bicyclic guanidine as catalyst and triethylamine as additive, the first asymmetric Michael addition of α-fluoro-β-ketoesters to various cyclic enones has been successfully developed, affording a variety of Michael adducts with potential synthetic utilities with satisfactory stereoselectivity (up to 94 % ee and 4.3 : 1 dr).

Publisher

CSIRO Publishing

Subject

General Chemistry

Link

http://www.publish.csiro.au/CH/pdf/CH14187

Reference12 articles.

1. Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

2. Enantioselective Construction of Quaternary Stereocenters

3. Binaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase-Transfer Catalysts: Asymmetric Amination of β-Keto Esters

4. Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles

5. Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles

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