Theoretical study of the thio-Claisen rearrangement. Can vinylthioethanimine undergo a [3,3]-sigmatropic shift?

1996 ◽  
pp. 2065-2071 ◽  
Author(s):  
Roger Arnaud ◽  
Valerie Dillet ◽  
Nadia Pelloux-Léon ◽  
Yannick Vallée
Keyword(s):  
Claisen Rearrangement ◽  
Theoretical Study ◽  
Sigmatropic Shift

Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1561-1575 ◽  
Author(s):  
Faiz Ahmed Khan ◽  
Mulla Althafh Hussain
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aldol Condensation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Account ◽  
Curcumin Analogues ◽  
Cross Coupling Reaction ◽  
Sigmatropic Shift ◽  
Novel Approaches

A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.

Unprecedented E-stereoselectivity on the sigmatropic Hurd–Claisen rearrangement of Morita–Baylis–Hillman adducts: a joint experimental–theoretical study

2019 ◽  
Vol 17 (18) ◽  
pp. 4498-4511 ◽  
Author(s):  
Vinicius Sobral Silva ◽  
Terezinha Alves Tolentino ◽  
Tiago Costa Alves Fontoura Rodrigues ◽  
Fernanda Ferrari Martins Santos ◽  
Daniel Francisco Scalabrini Machado ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Theoretical Study ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Non-covalent interactions as the origin of the stereoselectivity.

The role of cesium fluoride in aryl propargyl ether Claisen rearrangement and its mechanistic elucidation: a theoretical study

2016 ◽  
Vol 27 (5) ◽  
pp. 1383-1393 ◽  
Author(s):  
Mengistu Gemech Menkir ◽  
Venkatesan Srinivasadesikan ◽  
Shyi-Long Lee
Keyword(s):  
Claisen Rearrangement ◽  
Theoretical Study ◽  
Cesium Fluoride ◽  
Propargyl Ether
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