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One-Pot Dichotomous Construction of Inside-Azayohimban and Pro-Azayohimban Systems via an Enantioselective Organocatalytic Cascade; Their Use as a Model to Probe the (Aza-)Indole Local Solvent Environment

Author:
Yang, Van-Wei, Hong, Bor-Cherng, Kao, Hsin-Kai, Tu, Ting-Hsun, Shen, Jiun-Yi, Chen, Chi-Lin, Lee, Gene-Hsiang, Chou, Pi-Tai
Source:
Organic letters 2015 v.17 no.23 pp. 5816-5819
ISSN:
1523-7052
Subject:
catalytic activity, chemical reactions, enantioselective synthesis, enantioselectivity, models, moieties, organic compounds, proteins, solvents, tryptophan
Abstract:
A one-pot enantioselective synthesis of 7-azaindole-octahydroisoquinolin-3-one and an inside-aza-yohimbane system containing five contiguous stereogenic centers with high enantioselectivities (>99% ee) was achieved. The prepared highly functionalized polycyclic system provides a model for probing the solvent catalyzed proton transfer reaction and mimicking the local environment of the tryptophan moiety in proteins.
Agid:
5789967