Sterically Demanding Flexible Phosphoric Acids for Constructing Efficient and Multi-Purpose Asymmetric Organocatalysts.

Autor: Scharinger F; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Pálvölgyi ÁM; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Weisz M; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Weil M; Institute of Chemical Technologies and Analytics, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Stanetty C; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Schnürch M; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria., Bica-Schröder K; Institute of Applied Synthetic Chemistry, TU Wien Getreidemarkt 9/163 1060 Wien Austria.
Jazyk: angličtina
Zdroj: Angewandte Chemie (Weinheim an der Bergstrasse, Germany) [Angew Chem Weinheim Bergstr Ger] 2022 Jun 27; Vol. 134 (26), pp. e202202189. Date of Electronic Publication: 2022 Apr 26.
DOI: 10.1002/ange.202202189
Abstrakt: Herein, we present a novel approach for various asymmetric transformations of cyclic enones. The combination of readily accessible chiral diamines and sterically demanding flexible phosphoric acids resulted in a simple and highly tunable catalyst framework. The careful optimization of the catalyst components led to the identification of a particularly powerful and multi-purpose organocatalyst, which was successfully applied for asymmetric epoxidations, aziridinations, aza-Michael-initiated cyclizations, as well as for a novel Robinson-like Michael-initiated ring closure/aldol cyclization. High catalytic activities and excellent stereocontrol was observed for all four reaction types, indicating the excellent versatility of our catalytic system. Furthermore, a simple change in the diamine's configuration provided easy access to both product antipodes in all cases.
Competing Interests: The authors declare no conflict of interest.
(© 2022 The Authors. Angewandte Chemie published by Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje