An Asymmetric Michael Addition of α,α-Disubstituted Aldehydes to Maleimides Leading to a One-Pot Enantioselective Synthesis of Lactones Catalyzed by Amino Acids

2013 ◽  
Vol 15 (10) ◽  
pp. 2406-2409 ◽  
Author(s):  
Christoforos G. Kokotos
Keyword(s):  
Amino Acids ◽  
Michael Addition ◽  
Enantioselective Synthesis ◽  
One Pot ◽  
Asymmetric Michael Addition

scholarly journals Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a one-pot Sequential Asymmetric Michael addition/retro-Dieckmann/retro-Michael Fragmentation Cascade

2020 ◽  
Author(s):  
Nicolas Duchemin ◽  
Martin Cattoen ◽  
Oscar Gayraud ◽  
Silvia Anselmi ◽  
Bilal Siddiq ◽  
...  
Keyword(s):  
Michael Addition ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Direct Access ◽  
One Pot ◽  
Asymmetric Michael Addition ◽  
Wide Range

A highly enantioselective synthesis of a-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable and commercially available acrylonitrile surrogate, is practical, scalable, highly versatile, and provides a direct access to a wide range of enantioenriched nitrile-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.<br>

ChemInform Abstract: Highly Enantioselective Synthesis of α-Fluoro-α-nitro Esters via Organocatalyzed Asymmetric Michael Addition.

ChemInform ◽  
2011 ◽  
Vol 42 (16) ◽  
pp. no-no
Author(s):  
Hai-Feng Cui ◽  
Peng Li ◽  
Xiao-Wei Wang ◽  
Zhuo Chai ◽  
Ying-Quan Yang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Enantioselective Synthesis ◽  
Asymmetric Michael Addition ◽  
Nitro Esters

scholarly journals Efficient Asymmetric Synthesis of Prostaglandin E1

2007 ◽  
Vol 62 (4) ◽  
pp. 556-560 ◽  
Author(s):  
Jae-Chul Jung ◽  
Oee-Sook Park
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Prostaglandin E1 ◽  
Simple Synthesis ◽  
High Yield ◽  
Prostaglandin E ◽  
Magnesium Bromide ◽  
One Pot ◽  
Asymmetric Michael Addition ◽  
Key Steps

A simple synthesis of prostaglandin E1 (PGE1) is described. The key steps are an asymmetric Michael addition to establish the desired (R)-configurations at C8 and C12 of the 2- (trimethylsilyl)ethoxymethyl- (SEM) protected PGE1 and its one-pot deprotection with magnesium bromide in high yield. This method is potentially useful for the preparation of other modified prostaglandins.

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