A FACILE ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED ALKANOIC ACID THE HIGHLY STEREOSELECTIVE MICHAEL ADDITION OF GRIGNARD REAGENTS TO α,β-UNSATURATED CARBOXYLIC AMIDES DERIVED FROM L-EPHEDRINE

1981 ◽  
Vol 10 (7) ◽  
pp. 913-916 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Nobuharu Iwasawa
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Grignard Reagents ◽  
Alkanoic Acid

scholarly journals Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents

2019 ◽  
Vol 25 (1) ◽  
pp. 116-121
Author(s):  
Wei Zhou ◽  
Qingwei Xiao ◽  
Yuanyuan Chang ◽  
Qifa Liu ◽  
Xiaohao Zang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Chiral Auxiliary ◽  
Grignard Reagents ◽  
Amino Acid Derivatives ◽  
Catalyst Free ◽  
Chemical Efficiency

AbstractHerein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.

scholarly journals Functionalized main-group organometallics for organic synthesis

2002 ◽  
Vol 74 (1) ◽  
pp. 11-17 ◽  
Author(s):  
Paul Knochel ◽  
Eike Hupe ◽  
Wolfgang Dohle ◽  
David M. Lindsay ◽  
Véronique Bonnet ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Exchange Reaction ◽  
Organic Synthesis ◽  
Michael Addition ◽  
Main Group ◽  
Sigmatropic Rearrangement ◽  
Phosphine Ligands ◽  
Grignard Reagents ◽  
Chiral Phosphine Ligands

Highly functionalized Grignard-reagents can be easily obtained by an iodine­magnesim exchange reaction and further reacted with various electrophiles. Via a B­Zn exchange reaction, a formal Michael addition with umpolung of the reactivity can be achieved. Chiral phosphine ligands can be easily synthesized by a 2.3 sigmatropic rearrangement and used successfully in asymmetric synthesis.

Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization

2016 ◽  
Vol 22 (46) ◽  
pp. 16429-16432 ◽  
Author(s):  
Yuki Kaji ◽  
Naohiro Uemura ◽  
Yoshio Kasashima ◽  
Hiroki Ishikawa ◽  
Yasushi Yoshida ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Acid Derivative ◽  
Michael Addition ◽  
Amino Acid Derivative
Sign in / Sign up

Export Citation Format

Share Document