The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis. The methodology enables the realization of alpha-beta unsaturated, beta-thio, gamma-allyl carboxylic acid derivatives via a one-pot Lewis acid promoted Michael addition/[3,3]-sigmatropic rearrangement sequence (20 examples) in high yields (up to 95%). Full rationalization of the reaction mechanism and stereochemical outcome is provided via DFT simulations
Scandium catalysed stereoselective thio-allylation of allenyl-imidates / Adriano Parodi, Simone Battaglioli, Yang Liu, Magda Monari, Marta Marin-Luna, Carlos Silva-Lopez, Marco Bandini,. - In: CHEMICAL COMMUNICATIONS. - ISSN 1364-548X. - ELETTRONICO. - 55:(2019), pp. 9669-9672. [10.1039/c9cc04302k]
Scandium catalysed stereoselective thio-allylation of allenyl-imidates
Adriano ParodiMethodology
;Simone BattaglioliMethodology
;Yang LiuMethodology
;Magda MonariMethodology
;Marco Bandini
Conceptualization
2019
Abstract
The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis. The methodology enables the realization of alpha-beta unsaturated, beta-thio, gamma-allyl carboxylic acid derivatives via a one-pot Lewis acid promoted Michael addition/[3,3]-sigmatropic rearrangement sequence (20 examples) in high yields (up to 95%). Full rationalization of the reaction mechanism and stereochemical outcome is provided via DFT simulationsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
