Enantioselective One-Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

2010 ◽  
Vol 2010 (29) ◽  
pp. 5666-5671 ◽  
Author(s):  
Radovan Šebesta ◽  
Filip Bilčík ◽  
Peter Fodran
Keyword(s):  
Mannich Reaction ◽  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot

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

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].

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.

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

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

scholarly journals Tandem Fries Reaction–Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones

1999 ◽  
Vol 23 (9) ◽  
pp. 574-575
Author(s):  
Firouz Matloubi Moghaddam ◽  
Mohammad Ghaffarzadeh ◽  
Seyed Hossein Abdi-Oskoui
Keyword(s):  
Microwave Irradiation ◽  
Silica Gel ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Naphthalene Derivatives ◽  
One Pot ◽  
Fries Rearrangement ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Fries Reaction

An AICl3–ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.

Sign in / Sign up

Export Citation Format

Share Document