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
Adriano Parodi, S.B. (2019). Scandium catalysed stereoselective thio-allylation of allenyl-imidates. CHEMICAL COMMUNICATIONS, 55, 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 simulationsFile in questo prodotto:
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