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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

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posted on 04.12.2015, 00:00 by Van-Wei Yang, Bor-Cherng Hong, Hsin-Kai Kao, Ting-Hsun Tu, Jiun-Yi Shen, Chi-Lin Chen, Gene-Hsiang Lee, Pi-Tai Chou
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.