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The Diastereoselective Formation of Tetraalkoxy[4]resorcinarenes Derived from (–)‐(2 R )‐2‐Methoxy‐2‐phenylethanol and Proof of Absolute Configurations
Author(s) -
Bulman Page Philip C.,
Chan Yohan,
Heaney Harry,
McGrath Matthew J.,
Moreno Eduardo
Publication year - 2011
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/ejoc.201100733
Subject(s) - chemistry , steric effects , absolute configuration , resorcinol , ring (chemistry) , absolute (philosophy) , stereochemistry , phenol , stereoselectivity , alkyl , medicinal chemistry , organic chemistry , catalysis , philosophy , epistemology
The preparation of optically pure (–)‐3‐[(2 R )‐2‐methoxy‐2‐phenylethoxy]phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3‐alkoxyphenol.