A New Class of Non-Racemic Chiral Macrocycles: A Conformational and Synthetic Study

✍ Scribed by Susan E. Gibson; Nello Mainolfi; S. Barret Kalindjian; Paul T. Wright; Andrew J. P. White

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 468 KB
• Volume: 11
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200400608

✦ Synopsis

Abstract

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.