1,1′-Methylene-bis(1,1′,2,2′,3,3′,4, 4′-octahydroisoquinoline): Synthesis, reaction, resolution, and application in catalytic enantioselective transformations

Qiong Ji Yao; Zaher M.A. Judeh

doi:10.1016/j.tet.2011.04.004

1,1′-Methylene-bis(1,1′,2,2′,3,3′,4, 4′-octahydroisoquinoline): Synthesis, reaction, resolution, and application in catalytic enantioselective transformations

Qiong Ji Yao, Zaher M.A. Judeh

Nanyang Technological University

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

25 Citations (Scopus)

Abstract

The preparation of new chiral 1,3-diamine ligand systems based on the 1,1′-methylene-bis(1,1′,2,2′,3,3′,4,4′- octahydroisoquinoline) framework is described. Synthesis of various mono-, di-, and bridged N-alkyl derivatives are presented. Resolution of one compound, its Cu(I)Br X-ray crystallographic structure and the preliminary results on its application in the enantioselective Henry and Aldol reactions are disclosed.

Original language	English
Pages (from-to)	4086-4092
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2011.04.004
Publication status	Published - Jun 3 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Aldol reaction
Bisisoquinoline
C-C bond formation
Chiral 1,3-diamines
Copper bromide
Henry reaction

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10.1016/j.tet.2011.04.004

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abstract = "The preparation of new chiral 1,3-diamine ligand systems based on the 1,1′-methylene-bis(1,1′,2,2′,3,3′,4,4′- octahydroisoquinoline) framework is described. Synthesis of various mono-, di-, and bridged N-alkyl derivatives are presented. Resolution of one compound, its Cu(I)Br X-ray crystallographic structure and the preliminary results on its application in the enantioselective Henry and Aldol reactions are disclosed.",

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T1 - 1,1′-Methylene-bis(1,1′,2,2′,3,3′,4, 4′-octahydroisoquinoline)

T2 - Synthesis, reaction, resolution, and application in catalytic enantioselective transformations

AU - Yao, Qiong Ji

AU - Judeh, Zaher M.A.

PY - 2011/6/3

Y1 - 2011/6/3

N2 - The preparation of new chiral 1,3-diamine ligand systems based on the 1,1′-methylene-bis(1,1′,2,2′,3,3′,4,4′- octahydroisoquinoline) framework is described. Synthesis of various mono-, di-, and bridged N-alkyl derivatives are presented. Resolution of one compound, its Cu(I)Br X-ray crystallographic structure and the preliminary results on its application in the enantioselective Henry and Aldol reactions are disclosed.

AB - The preparation of new chiral 1,3-diamine ligand systems based on the 1,1′-methylene-bis(1,1′,2,2′,3,3′,4,4′- octahydroisoquinoline) framework is described. Synthesis of various mono-, di-, and bridged N-alkyl derivatives are presented. Resolution of one compound, its Cu(I)Br X-ray crystallographic structure and the preliminary results on its application in the enantioselective Henry and Aldol reactions are disclosed.

KW - Aldol reaction

KW - Bisisoquinoline

KW - C-C bond formation

KW - Chiral 1,3-diamines

KW - Copper bromide

KW - Henry reaction

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SP - 4086

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JO - Tetrahedron

JF - Tetrahedron

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1,1′-Methylene-bis(1,1′,2,2′,3,3′,4, 4′-octahydroisoquinoline): Synthesis, reaction, resolution, and application in catalytic enantioselective transformations

Abstract

ASJC Scopus Subject Areas

Keywords

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