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

Raju Nandhakumar; Ahn Yun Soo; Jooyeon Hong; Sihyun Ham; Kwan Mook Kim

doi:10.1016/j.tet.2008.11.022

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

Raju Nandhakumar, Ahn Yun Soo, Jooyeon Hong, Sihyun Ham, Kwan Mook Kim

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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 ¹H NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and pyrrolyl groups.

Original language	English
Pages (from-to)	666-671
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	3
DOIs	https://doi.org/10.1016/j.tet.2008.11.022
State	Published - 17 Jan 2009

Bibliographical note

Funding Information:
This work was supported by the Ministry of Science & Technology of Korea through NRL (R0A-2006-000-10269-0), SRC program of KOSEF (R11-2005-008-000000), KRF (2004-005-C00093), and R01-2006-10696 from the Korea Science and Engineering Foundation.

Keywords

Aminoalcohol
Enantioselective recognition
Pyrrole-2-carboxamide

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10.1016/j.tet.2008.11.022

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

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 1H NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and pyrrolyl groups.",

keywords = "Aminoalcohol, Enantioselective recognition, Pyrrole-2-carboxamide",

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note = "Funding Information: This work was supported by the Ministry of Science & Technology of Korea through NRL (R0A-2006-000-10269-0), SRC program of KOSEF (R11-2005-008-000000), KRF (2004-005-C00093), and R01-2006-10696 from the Korea Science and Engineering Foundation.",

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AU - Soo, Ahn Yun

AU - Hong, Jooyeon

AU - Ham, Sihyun

AU - Kim, Kwan Mook

N1 - Funding Information: This work was supported by the Ministry of Science & Technology of Korea through NRL (R0A-2006-000-10269-0), SRC program of KOSEF (R11-2005-008-000000), KRF (2004-005-C00093), and R01-2006-10696 from the Korea Science and Engineering Foundation.

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N2 - 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 1H NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and pyrrolyl groups.

AB - 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 1H NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and pyrrolyl groups.

KW - Aminoalcohol

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

Abstract

Bibliographical note

Keywords

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