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

Van-Wei Yang; Bor-Cherng Hong; Hsin-Kai Kao; Ting-Hsun Tu; Jiun-Yi Shen; Chi-Lin Chen; Gene-Hsiang Lee; Pi-Tai Chou

doi:10.1021/acs.orglett.5b02949

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

Org Lett. 2015 Dec 4;17(23):5816-9. doi: 10.1021/acs.orglett.5b02949. Epub 2015 Nov 20.

Authors

Van-Wei Yang¹, Bor-Cherng Hong¹, Hsin-Kai Kao¹, Ting-Hsun Tu², Jiun-Yi Shen², Chi-Lin Chen², Gene-Hsiang Lee², Pi-Tai Chou²

Affiliations

¹ Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan, R.O.C.
² Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.

PMID: 26584631
DOI: 10.1021/acs.orglett.5b02949

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Crystallography, X-Ray
Indoles / chemical synthesis*
Indoles / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Molecular Conformation
Molecular Structure
Proteins / chemistry
Solvents
Stereoisomerism
Tryptophan / chemistry

Substances

7-azaindole-octahydroisoquinolin-3-one
Indoles
Isoquinolines
Proteins
Solvents
Tryptophan