1-Alkynyl(aryl)(tetrafluoroborato)-?3-bromanes as Highly Efficient Michael Acceptors: Uncatalyzed Conjugate Addition of 1-Alkynyl(trialkyl)stannanes To Yield Symmetrical and Unsymmetrical 1,3-Butadiynes

2005 ◽  
Vol 44 (3) ◽  
pp. 406-409 ◽  
Author(s):  
Masahito Ochiai ◽  
Yoshio Nishi ◽  
Satoru Goto ◽  
Hermann J. Frohn
Keyword(s):  
Conjugate Addition ◽  
Highly Efficient ◽  
Michael Acceptors

Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: a Powerful Synthetic Platform

2015 ◽  
Vol 127 (40) ◽  
pp. 11996-12000 ◽  
Author(s):  
Sammy Drissi-Amraoui ◽  
Marie S. T. Morin ◽  
Christophe Crévisy ◽  
Olivier Baslé ◽  
Renata Marcia de Figueiredo ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Michael Acceptors

scholarly journals Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors

2017 ◽  
Vol 8 (2) ◽  
pp. 1613-1620 ◽  
Author(s):  
Andrea Gualandi ◽  
Elia Matteucci ◽  
Filippo Monti ◽  
Andrea Baschieri ◽  
Nicola Armaroli ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Conjugate Addition ◽  
Michael Acceptors

An iridium(iii) phenyl-tetrazole complex is a versatile catalyst for a new photocatalytic Michael reaction.

scholarly journals NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center

Catalysts ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 192 ◽  
Author(s):  
Zbigniew Rafiński
Keyword(s):  
Stetter Reaction ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Michael Acceptors ◽  
High Yields ◽  
Stereogenic Center ◽  
Quaternary Stereogenic Centers ◽  
Triazolium Salts

A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived triazolium salts. As a result, a series of chiral 2,2-disubstituted benzofuran-3(2H)-one derivatives with linear, branched, and cyclic aliphatic substitutions on the quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities of up to 99% ee.

scholarly journals Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

2020 ◽  
Vol 16 ◽  
pp. 212-232 ◽  
Author(s):  
Delphine Pichon ◽  
Jennifer Morvan ◽  
Christophe Crévisy ◽  
Marc Mauduit
Keyword(s):  
Natural Products ◽  
Conjugate Addition ◽  
Catalytic Transformation ◽  
Chiral Molecules ◽  
Catalytic Systems ◽  
Organometallic Reagents ◽  
Recent Advances ◽  
Wide Range ◽  
Michael Acceptors

The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.

Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(iii) complex

2017 ◽  
Vol 4 (4) ◽  
pp. 573-577 ◽  
Author(s):  
Tao Deng ◽  
Ganesh Kumar Thota ◽  
Yi Li ◽  
Qiang Kang
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Conjugate Addition ◽  
Amino Acid Derivatives ◽  
Highly Efficient

A highly efficient chiral-at-metal Rh(iii) complex catalyzed asymmetric aza-Michael addition was developed, affordingN-protected β-amino acid derivatives with excellent enantioselectivity.

Highly efficient procedure for the conjugate addition of amines to electron deficient alkenes

2010 ◽  
Vol 51 (2) ◽  
pp. 225-228 ◽  
Author(s):  
An-ping Liao ◽  
Ping Lan ◽  
Mei Li ◽  
Li-hong Lan
Keyword(s):  
Conjugate Addition ◽  
Efficient Procedure ◽  
Highly Efficient
Sign in / Sign up

Export Citation Format

Share Document