A Facile and Stereocontrolled Synthesis of γ-Substituted γ-Fluoroglutamates by Conjugate Addition: Conflicting Effect between Fluorinated Enaminoester and Hinderered Michael Acceptor

2010 ◽  
Vol 75 (22) ◽  
pp. 7596-7604 ◽  
Author(s):  
Emmanuelle Drège ◽  
Anaïs Guillaume ◽  
Nadjia Boukhedimi ◽  
Jérôme Marrot ◽  
Claire Troufflard ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Stereocontrolled Synthesis ◽  
Michael Acceptor

scholarly journals Lewis Acid Promoted Trapping of Chiral Aza-enolates

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1253-1262
Author(s):  
Francesco Lanza ◽  
Juana Pérez ◽  
Ravindra Jumde ◽  
Syuzanna Harutyunyan
Keyword(s):  
Lewis Acid ◽  
Conjugate Addition ◽  
Conventional Wisdom ◽  
Grignard Reagents ◽  
One Pot ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Reactivity Order

We present a study on sequential conjugate addition of ­Grignard reagents to alkenyl-heteroarenes followed by trapping of the resulting enolates, yielding moderate to good diastereoselectivities. Contrary to conventional wisdom, one-pot conjugate addition/trapping using two reactive Michael acceptors in combination with Grignard reagents can proceed via conjugate addition to the least reactive Michael acceptor. This unusual chemoselectivity is triggered by the presence of a Lewis acid, reverting the usual reactivity order of Michael acceptors.

ChemInform Abstract: Expedient Synthesis of 3,4-Dihydroquinazolines via Tandem Addition-Conjugate Addition Cyclization of Carbodiimides Bearing a Michael Acceptor.

ChemInform ◽  
2012 ◽  
Vol 43 (22) ◽  
pp. no-no
Author(s):  
Takao Saito ◽  
Hayato Nakano ◽  
Hidenori Terada ◽  
Noriki Kutsumura ◽  
Takashi Otani
Keyword(s):  
Conjugate Addition ◽  
Michael Acceptor

Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

2016 ◽  
Vol 52 (8) ◽  
pp. 1697-1700 ◽  
Author(s):  
Claudia Del Fiandra ◽  
Maria Moccia ◽  
Valentina Cerulli ◽  
Mauro F. A. Adamo
Keyword(s):  
Ethyl Ester ◽  
Quaternary Ammonium ◽  
Conjugate Addition ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Catalytic Asymmetric

Un-substituted isocyanoacetate ethyl ester reacted with Michael acceptors 1a–m under the catalysis of Cinchona based quaternary ammonium salts providing imines 4a–m as a single diastereoisomer and in up to 94% ees.

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