Synthesis of Chiral Tetrahydroisoquinoline and C 2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction

Duc Thinh Khong; Zaher M.A. Judeh

doi:10.1055/s-0035-1561634

Synthesis of Chiral Tetrahydroisoquinoline and C ₂-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction

Duc Thinh Khong, Zaher M.A. Judeh^*

^*Corresponding author for this work

Nanyang Technological University

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

3 Citations (Scopus)

Abstract

Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as ligands in the enantioselective Henry reaction. The conformational rigidity of these ligands and the size of the coordination sphere control the enantioselectivity of the products. The conformationally rigid chiral tetrahydroisoquinoline THIQ-Cu(OAc)₂·H₂O complex successfully catalyzed the enantioselective Henry reaction between various aldehydes and nitromethane and gives the β-nitro alcohol adducts in up to 96% yield and 80% ee.

Original language	English
Article number	ss-2015-n0661-op
Pages (from-to)	2271-2279
Number of pages	9
Journal	Synthesis
Volume	48
Issue number	14
DOIs	https://doi.org/10.1055/s-0035-1561634
Publication status	Published - Jul 15 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© Georg Thieme Verlag Stuttgart - New York.

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

asymmetric catalysis
bistetrahydroisoquinoline
C -symmetric ligand
Henry reaction
tetrahydroisoquinoline

Access to Document

10.1055/s-0035-1561634

Cite this

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title = "Synthesis of Chiral Tetrahydroisoquinoline and C 2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction",

abstract = "Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as ligands in the enantioselective Henry reaction. The conformational rigidity of these ligands and the size of the coordination sphere control the enantioselectivity of the products. The conformationally rigid chiral tetrahydroisoquinoline THIQ-Cu(OAc)2·H2O complex successfully catalyzed the enantioselective Henry reaction between various aldehydes and nitromethane and gives the β-nitro alcohol adducts in up to 96% yield and 80% ee.",

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T1 - Synthesis of Chiral Tetrahydroisoquinoline and C 2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction

AU - Khong, Duc Thinh

AU - Judeh, Zaher M.A.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart - New York.

PY - 2016/7/15

Y1 - 2016/7/15

N2 - Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as ligands in the enantioselective Henry reaction. The conformational rigidity of these ligands and the size of the coordination sphere control the enantioselectivity of the products. The conformationally rigid chiral tetrahydroisoquinoline THIQ-Cu(OAc)2·H2O complex successfully catalyzed the enantioselective Henry reaction between various aldehydes and nitromethane and gives the β-nitro alcohol adducts in up to 96% yield and 80% ee.

AB - Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as ligands in the enantioselective Henry reaction. The conformational rigidity of these ligands and the size of the coordination sphere control the enantioselectivity of the products. The conformationally rigid chiral tetrahydroisoquinoline THIQ-Cu(OAc)2·H2O complex successfully catalyzed the enantioselective Henry reaction between various aldehydes and nitromethane and gives the β-nitro alcohol adducts in up to 96% yield and 80% ee.

KW - asymmetric catalysis

KW - bistetrahydroisoquinoline

KW - C -symmetric ligand

KW - Henry reaction

KW - tetrahydroisoquinoline

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