Synthesis of Azaylide‐Based Amphiphiles by Staudinger Reaction

2021 ◽  
Author(s):  
Masahiro Yamashina ◽  
Hayate Suzuki ◽  
Natsuki Kishida ◽  
Michito Yoshizawa ◽  
Shinji Toyota
Keyword(s):  
Staudinger Reaction

scholarly journals Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2177
Author(s):  
Antonia Di Mola ◽  
Consiglia Tedesco ◽  
Antonio Massa
Keyword(s):  
Heterocyclic Compounds ◽  
Aromatic Ketone ◽  
Primary Amines ◽  
Cascade Process ◽  
Staudinger Reaction ◽  
Caspase Inhibitor ◽  
Air Oxidation ◽  
Metal Free ◽  
Free Air

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to a series of isoquinoline-1,3,4(2H)-triones, a class of heterocyclic compounds of great interest containing an oxygen-rich heterocyclic scaffold. A modification of the original protocol, utilizing a Staudinger reaction in the presence of trimethylphosphine, was necessary for the synthesis of Caspase inhibitor trione with free NH group.

scholarly journals Practical synthesis of 4-aryl- and 4-heteroarylazetidin-2-ones: applications in the synthesis of the Taxol® side chain

1994 ◽  
Vol 72 (10) ◽  
pp. 2131-2136 ◽  
Author(s):  
Allan W. Rey ◽  
Robert Droghini ◽  
James L. Douglas ◽  
Purushotham Vemishetti ◽  
Susan D. Boettger ◽  
...  
Keyword(s):  
Side Chain ◽  
Staudinger Reaction ◽  
Protecting Group ◽  
Practical Synthesis

A convenient, high-yielding procedure has been developed for the kilogram-scale synthesis of (±)-cis-3-acetoxy-4-phenylazetidin-2-one (3), a β-lactam that has been used in the semi-synthesis of Taxol®. The Staudinger reaction between hydrobenzamide (5) and acetoxyacetyl chloride in the presence of a base provided the α-benzylideneiminotoluene protected β-lactam 8. Without isolation of the intermediate β-lactam, the protecting group was removed under various reductive or hydrolytic conditions. The overall yields were about 80%. The synthesis of other (±)-cis-4-aryl- and 4-heteroarylazetidin-2-ones by this methodology has also been accomplished. These compounds are of value for the synthesis of 3′-Taxol® side-chain analogs and their preparation demonstrates the generality of this approach.

ChemInform Abstract: Stereocontrolled Synthesis of β-Lactams via Staudinger Reaction Between Phenoxyketenes and Chiral Imines.

ChemInform ◽  
2010 ◽  
Vol 33 (19) ◽  
pp. no-no
Author(s):  
Seema Kanwar ◽  
Aarti Saluja ◽  
J. P. S. Khurana ◽  
S. D. Sharma
Keyword(s):  
Staudinger Reaction ◽  
Stereocontrolled Synthesis ◽  
Chiral Imines

Synthesis of β-Lactams from aN-Rhenaimine:  Effect of the Transition Metal on the Energetic Profile of the Staudinger Reaction

2003 ◽  
Vol 125 (13) ◽  
pp. 3706-3707 ◽  
Author(s):  
Eva Hevia ◽  
Julio Pérez ◽  
Víctor Riera ◽  
Daniel Miguel ◽  
Pablo Campomanes ◽  
...  
Keyword(s):  
Transition Metal ◽  
Staudinger Reaction

Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams

2016 ◽  
Vol 57 (46) ◽  
pp. 5084-5088 ◽  
Author(s):  
Ankita Rai ◽  
Puneet K. Singh ◽  
Prashant Shukla ◽  
Vijai K. Rai
Keyword(s):  
Carboxylic Acid ◽  
Stereoselective Synthesis ◽  
Acid Activation ◽  
Staudinger Reaction
Sign in / Sign up

Export Citation Format

Share Document