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Enantioselective recognition of 1,2-aminoalcohols by the binol receptor dangled with pyrrole-2-carboxamide and its analogues

Authors
Nandhakumar, RajuSoo, Ahn YunHong, JooyeonHam, SihyunKim, Kwan Mook
Issue Date
Jan-2009
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
Enantioselective recognition; Aminoalcohol; Pyrrole-2-carboxamide
Citation
TETRAHEDRON, v.65, no.3, pp.666 - 671
Journal Title
TETRAHEDRON
Volume
65
Number
3
Start Page
666
End Page
671
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/13837
DOI
10.1016/j.tet.2008.11.022
ISSN
0040-4020
Abstract
Novel binol receptor with pyrrole-2-carboxamide moiety and its analogues have been designed, synthesized, and used to enantioselectively recognize 1,2-aminoalcohols via multiple hydrogen bonding. The pyrrole-based binol receptor showed the highest enantioselectivity among the four receptors as determined by the H-1 NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and Pyrrolyl groups. (c) 2008 Elsevier Ltd. All rights reserved.
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