Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generatedo-Quinone Methides

Meisinger, Nicole; Roiser, Lukas; Monkowius, Uwe; Himmelsbach, Markus; Robiette, Raphaël; Waser, Mario

doi:10.1002/chem.201700171

Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generatedo-Quinone Methides

Meisinger, Nicole

;

Roiser, Lukas

;

Monkowius, Uwe

;

Himmelsbach, Markus

;

Waser, Mario

;et.al.

(2017) Chemistry: A European Journal — Vol. 23, n° 21, p. 5137-5142 (2017)

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Authors

Meisinger, Nicole
Author
Roiser, Lukas
Author
Monkowius, Uwe
Author
Himmelsbach, Markus
Author
Robiette, RaphaëlUCLouvain
Author
Waser, Mario
Author

Abstract

A highly enantio- and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o-quinone methides for the synthesis of a variety of 2,3-dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by experimental and computational means and the energy profiles obtained provide a deeper insight into the mechanistic details of this reaction.

Affiliations

UCLouvainSST/IMCN/MOST - Molecular Chemistry, Materials and Catalysis

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Meisinger, N., Roiser, L., Monkowius, U., Himmelsbach, M., Robiette, R., & Waser, M. (2017). Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generatedo-Quinone Methides. Chemistry: A European Journal, 23(21), 5137-5142. https://doi.org/10.1002/chem.201700171 (Original work published 2017)