New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

Hoi Lun Kwong; Wing Leung Wong; Wing Sze Lee; Leung Shi Cheng; Wing Tak Wong

doi:10.1016/S0957-4166(01)00431-1

New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

Hoi Lun Kwong, Wing Leung Wong, Wing Sze Lee, Leung Shi Cheng, Wing Tak Wong

Research output: Journal article publication › Journal article › Academic research › peer-review

48 Citations (Scopus)

Abstract

A number of chiral C2-symmetric 2,2′:6′,2″ terpyridines L1-L4were synthesized in moderate to good yields from commercially available chiral materials. Copper(II) and rhodium(III) chloride complexes of these ligands were prepared in good yields. The Rh(L2)Cl3complex was isolated as a yellow crystalline solid and characterized by X-ray crystallography. Both Cu(L)(OTf)2and Rh(L)(OTf)3were found to be active catalysts in the cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivity up to 82% e.e. was observed.

Original language	English
Pages (from-to)	2683-2694
Number of pages	12
Journal	Tetrahedron Asymmetry
Volume	12
Issue number	19
DOIs	https://doi.org/10.1016/S0957-4166(01)00431-1
Publication status	Published - 30 Oct 2001
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Kwong, H. L., Wong, W. L., Lee, W. S., Cheng, L. S., & Wong, W. T. (2001). New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene. Tetrahedron Asymmetry, 12(19), 2683-2694. https://doi.org/10.1016/S0957-4166(01)00431-1

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title = "New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene",

abstract = "A number of chiral C2-symmetric 2,2′:6′,2″ terpyridines L1-L4were synthesized in moderate to good yields from commercially available chiral materials. Copper(II) and rhodium(III) chloride complexes of these ligands were prepared in good yields. The Rh(L2)Cl3complex was isolated as a yellow crystalline solid and characterized by X-ray crystallography. Both Cu(L)(OTf)2and Rh(L)(OTf)3were found to be active catalysts in the cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivity up to 82% e.e. was observed.",

author = "Kwong, {Hoi Lun} and Wong, {Wing Leung} and Lee, {Wing Sze} and Cheng, {Leung Shi} and Wong, {Wing Tak}",

year = "2001",

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doi = "10.1016/S0957-4166(01)00431-1",

language = "English",

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New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene. / Kwong, Hoi Lun; Wong, Wing Leung; Lee, Wing Sze et al.
In: Tetrahedron Asymmetry, Vol. 12, No. 19, 30.10.2001, p. 2683-2694.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

AU - Kwong, Hoi Lun

AU - Wong, Wing Leung

AU - Lee, Wing Sze

AU - Cheng, Leung Shi

AU - Wong, Wing Tak

PY - 2001/10/30

Y1 - 2001/10/30

N2 - A number of chiral C2-symmetric 2,2′:6′,2″ terpyridines L1-L4were synthesized in moderate to good yields from commercially available chiral materials. Copper(II) and rhodium(III) chloride complexes of these ligands were prepared in good yields. The Rh(L2)Cl3complex was isolated as a yellow crystalline solid and characterized by X-ray crystallography. Both Cu(L)(OTf)2and Rh(L)(OTf)3were found to be active catalysts in the cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivity up to 82% e.e. was observed.

AB - A number of chiral C2-symmetric 2,2′:6′,2″ terpyridines L1-L4were synthesized in moderate to good yields from commercially available chiral materials. Copper(II) and rhodium(III) chloride complexes of these ligands were prepared in good yields. The Rh(L2)Cl3complex was isolated as a yellow crystalline solid and characterized by X-ray crystallography. Both Cu(L)(OTf)2and Rh(L)(OTf)3were found to be active catalysts in the cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivity up to 82% e.e. was observed.

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U2 - 10.1016/S0957-4166(01)00431-1

DO - 10.1016/S0957-4166(01)00431-1

M3 - Journal article

SN - 0957-4166

VL - 12

SP - 2683

EP - 2694

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 19

ER -

New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: Synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

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