Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Adriano Parodi; Simone Battaglioli; Yang Liu; Magda Monari; Marta Marín-Luna; Carlos Silva-López; Marco Bandini

doi:10.1039/C9CC04302K

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Scandium catalysed stereoselective thio-allylation of allenyl-imidates†

Adriano Parodi,^a Simone Battaglioli,^a Yang Liu,^a Magda Monari,

^a Marta Marín-Luna,^b Carlos Silva-López

*^b and Marco Bandini

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum, via Selmi 2, Bologna, Italy
E-mail: marco.bandini@unibo.it

^b Departmento de Química Organica, Univesidad de Vigo, 36310 Vigo, Spain
E-mail: carlos.silva@uvigo.es

Abstract

The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis. The methodology enables the realization of α-β unsaturated, β-thio, γ-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.

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DOI: https://doi.org/10.1039/C9CC04302K
Article type: Communication
Submitted: 04 Jun 2019
Accepted: 18 Jul 2019
First published: 25 Jul 2019

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Chem. Commun., 2019,55, 9669-9672

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Scandium catalysed stereoselective thio-allylation of allenyl-imidates

A. Parodi, S. Battaglioli, Y. Liu, M. Monari, M. Marín-Luna, C. Silva-López and M. Bandini, Chem. Commun., 2019, 55, 9669 DOI: 10.1039/C9CC04302K

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Chemical Communications

Scandium catalysed stereoselective thio-allylation of allenyl-imidates†

Abstract

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Scandium catalysed stereoselective thio-allylation of allenyl-imidates

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