Highly Efficient Atom‐Economic Synthesis of Chiral Bis(indolyl)methanes Bearing Quaternary Stereogenic Carbon Centers

A highly efficient atom‐economic method for the preparation of chiral 3,3′‐bis(indolyl)methanes (3,3′‐BIMs) was developed. A chiral phosphoric acid (1 mol %) was found to promote the formation of structurally divers BIMs with quaternary stereogenic carbon centers in excellent yields with excellent e...

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Published in:ChemCatChem 2017-08, Vol.9 (16), p.3107-3110
Main Authors: Zhang, Yan, Zhang, Si‐Xiang, Fu, Li‐Na, Guo, Qi‐Xiang
Format: Article
Language:English
Subjects:
asymmetric catalysis
atom economy
Brønsted acids
Catalysts
enantioselectivity
Hydrogen bonds
nitrogen heterocycles
Phosphoric acid
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description A highly efficient atom‐economic method for the preparation of chiral 3,3′‐bis(indolyl)methanes (3,3′‐BIMs) was developed. A chiral phosphoric acid (1 mol %) was found to promote the formation of structurally divers BIMs with quaternary stereogenic carbon centers in excellent yields with excellent enantioselectivities. Control experiments indicated that the simultaneous formation of two hydrogen bonds between the catalyst and the substrate was the key factor to obtain a good stereoselective outcome. Dol‐ing out: The chiral Brønsted acid catalyzed Friedel–Crafts reaction of 3‐vinylindole with substituted indoles is an efficient method to build chiral 3,3′‐bis(indolyl)methanes (BIMs). Structurally divers BIMs with quaternary stereogenic carbon centers are produced in excellent yields with excellent enantioselectivities.
doi_str_mv 10.1002/cctc.201700368
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subjects asymmetric catalysis
atom economy
Brønsted acids
Catalysts
enantioselectivity
Hydrogen bonds
nitrogen heterocycles
Phosphoric acid
title Highly Efficient Atom‐Economic Synthesis of Chiral Bis(indolyl)methanes Bearing Quaternary Stereogenic Carbon Centers
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