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Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
50
Issue
4
Identifiers
DOI: 10.1016/j.tetlet.2008.11.021

Abstract

Abstract Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, ( S)-2-amino-1-butanol and ( S)- tert-leucinol were found to be the most effective for CIAT of the corresponding bridged bisnicotinate 5b and 7, respectively, whose diastereomeric ratio finally reached 97% and 88%, respectively.

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