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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 2
BKCSDE 26(2)
February 20, 2005 

 
Title
Dynamic Resolution of α-Bromo Tertiary Amides for Stereoselective Preparation of Dipeptide Analogues
Author
Hyun Jung Kim, Ji-yeon Chang, Eun-kyoung Shin, Yong Sun Park*
Keywords
Dynamic resolution, Asymmetric syntheses, Nucleophilic substitution
Abstract
Dynamic resolution of α-bromo tertiary acetamides in asymmetric nucleophilic substitution reaction is described. Intermolecular substitution of α-bromo tertiary acetamides with dibenzylamine in the presence of TBAI and Et3N gave the dipeptide analogues 7-10 with high stereoselectivities up to 90 : 10 dr. Also, cyclic dipeptide analogues 20-29 were produced by the intramolecular nucleophilic cyclization of α-bromo tertiary acetamides with low stereoselectivities in 84-42% yields.
Page
273 - 277
Full Text
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