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First Synthesis, Isolation and Complete Characterization of Both Enantiomers of Inherently Chiral Resorc[4]arenes by Monofunctionalization
Author(s) -
Agena Ceno,
Wolff Christian,
Mattay Jochen
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:15<2977::aid-ejoc2977>3.0.co;2-l
Subject(s) - chemistry , diazomethane , diastereomer , enantiomer , hydrolysis , alkaline hydrolysis , chloride , stereochemistry , organic chemistry
The monofunctionalization of rccc ‐2,8,14,20‐tetramethylresorc[4]arene (1) with ( S )‐( + )‐10‐camphorsulfonyl chloride led to a diastereomeric mixture of (+)‐2a and (−)‐2b , which were separated by HPLC. Permethylation of these compounds was achieved with diazomethane. The inherently chiral, enantiomerically pure resorc[4]arenes (+)‐4 and (−)‐4 were obtained by alkaline hydrolysis of (+)‐3a or (+)‐3b , respectively.