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A New Class of Non‐Racemic Chiral Macrocycles: A Conformational and Synthetic Study
Author(s) -
Gibson Susan E.,
Mainolfi Nello,
Kalindjian S. Barret,
Wright Paul T.,
White Andrew J. P.
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400608
Subject(s) - class (philosophy) , stereochemistry , chemistry , combinatorial chemistry , computer science , artificial intelligence
Amino alcohols have been used to introduce non‐racemic chirality into macrocycles using a modular approach that relies on a Heck macrocyclisation reaction. A wide variety of macrocycles have been synthesised, and their structures studied using X‐ray crystallography and molecular modelling. A fragmentation reaction encountered during the use of ( S )‐1,1‐dimethylvalinol revealed that carboxylic acids generate acylals under reaction conditions often used for Heck reactions.