Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation

2011 ◽  
Vol 77 (1) ◽  
pp. 760-765 ◽  
Author(s):  
Filip Bilčík ◽  
Michal Drusan ◽  
Jozef Marák ◽  
Radovan Šebesta
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot ◽  
Cyclic Enones

ChemInform Abstract: Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation.

ChemInform ◽  
2012 ◽  
Vol 43 (18) ◽  
pp. no-no
Author(s):  
Filip Bilcik ◽  
Michal Drusan ◽  
Jozef Marak ◽  
Radovan Sebesta
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot ◽  
Cyclic Enones

Asymmetric One-Pot Conjugate Addition of Grignard Reagents to α,β-Unsaturated Compounds Followed by Reaction with Carbenium Ions

2015 ◽  
Vol 357 (7) ◽  
pp. 1493-1498 ◽  
Author(s):  
Michal Drusan ◽  
Erik Rakovský ◽  
Jaromír Marek ◽  
Radovan Šebesta
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot ◽  
Carbenium Ions ◽  
Unsaturated Compounds

scholarly journals Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence

RSC Advances ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 1783-1793
Author(s):  
Alexander V. Aksenov ◽  
Dmitrii A. Aksenov ◽  
Nicolai A. Aksenov ◽  
Anton A. Skomorokhov ◽  
Elena V. Aleksandrova ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot ◽  
Subsequent Acid

One-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and subsequent acid-assisted spirocyclization allowed for diastereoselective preparation of 4′H-spiro[indole-3,5′-isoxazoles].

Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones

2012 ◽  
Vol 18 (28) ◽  
pp. 8731-8747 ◽  
Author(s):  
Matthieu Tissot ◽  
Daniele Poggiali ◽  
Hélène Hénon ◽  
Daniel Müller ◽  
Laure Guénée ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
Addition Reactions ◽  
Stereogenic Centers ◽  
Cyclic Enones ◽  
Quaternary Stereogenic Centers

scholarly journals Asymmetric Catalysis Special Feature Part II: Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones

2004 ◽  
Vol 101 (16) ◽  
pp. 5834-5838 ◽  
Author(s):  
B. L. Feringa ◽  
R. Badorrey ◽  
D. Pena ◽  
S. R. Harutyunyan ◽  
A. J. Minnaard
Keyword(s):  
Asymmetric Catalysis ◽  
Conjugate Addition ◽  
Grignard Reagents ◽  
Cyclic Enones

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.

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