Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition

Angewandte Chemie
Coralie GelisGéraldine Masson

Abstract

A highly enantio- and diastereoselective formal (4+3) cycloaddition of 1,3-diene-1-carbamates with 3-indolylmethanols in the presence of a chiral phosphoric acid catalyst is reported. The approach described herein provides efficient access to 6-aminotetrahydrocyclohepta[b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (>98:2 dr and up to 98 % ee). Mild reaction conditions, facile scale-up, and versatile derivatization highlight the practicality of this methodology. A mechanistic study suggests that cycloaddition occurs in a stepwise fashion, after the formation of an ion pair between the chiral catalytic phosphate and the intermediate carbocation.

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Citations

May 29, 2020·Chemistry : a European Journal·Dina Christina TymannMartin Hiersemann
Jun 11, 2020·Chemistry, an Asian Journal·Karuppu SelvarajK C Kumara Swamy
Jun 4, 2020·Chemistry : a European Journal·Susana Estopiñá-Durán, James E Taylor
Feb 14, 2019·Bioorganic & Medicinal Chemistry·Thomas VarletGéraldine Masson
Apr 29, 2021·Chemical Communications : Chem Comm·Thomas Varlet, Géraldine Masson
Jul 24, 2021·Journal of the American Chemical Society·Thomas VarletGéraldine Masson
Sep 15, 2020·The Journal of Organic Chemistry·Lance T Lepovitz, Stephen F Martin
Jan 15, 2022·Organic Letters·Isaiah O BetinolJolene P Reid

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