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Catalytic Asymmetric Cascade Cyclization for Constructing Three Contiguous Stereocenters in Pyrrolobenzodiazepine-Based Cyclopentanones

Author:
Wei, Zhao, Zhang, Jinlong, Yang, Huameng, Jiang, Gaoxi
Source:
Organic letters 2019 v.21 no.8 pp. 2790-2794
ISSN:
1523-7052
Subject:
Bronsted acids, alkylation, chemical structure, cyclization reactions, diastereoselectivity, enantioselectivity, pyrroles, stereochemistry
Abstract:
A chiral Brønsted acid catalyzed highly enantio- and diastereoselective cascade cyclization has been developed to streamline the synthesis of valuable multifunctionalized enantioenriched cyclopenta[f]pyrrolo[1,2-d][1,4]diazepinones bearing three contiguous stereocenters in high yields with excellent control of stereochemistry from a wide range of both readily available 2-furylcarbinols and (1H-pyrrol-1-yl)anilines, which represents the first asymmetric intramolecular conjugate addition of α,β-unsaturated cycloketones with inert N-substituted pyrroles as well as the first enantioselective aza-piancatelli rearrangement/Friedel–Crafts alkylation cascade reaction.
Agid:
6375963