Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo[a, c]cycloheptadiene bis(oxazoline) metal complexes

Bin Fu; Da Ming Du

doi:10.1002/cjoc.20030210603

Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo[a, c]cycloheptadiene bis(oxazoline) metal complexes

Bin Fu^*, Da Ming Du

^*Corresponding author for this work

Peking University

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

10 Citations (Scopus)

Abstract

A series of novel chiral C₂-symmetric bis (oxazoline) ligands have been synthesized. The copper and magnesium complexes, prepared in situ from copper (II)-triflate or magnesium triflate with the new enantiopure oxazoline ligands, were evaluated as chiral catalysts in the enantioselective Diels-Alder reaction of cyclopentadiene with N-crotenoyl-oxazolidin-2-one. Primary results showed that diastereoselectivity up to 94% and enantioselectivity up to 68% ee for endo products were observed respectively with these ligands.

Original language	English
Pages (from-to)	597-599
Number of pages	3
Journal	Chinese Journal of Chemistry
Volume	21
Issue number	6
DOIs	https://doi.org/10.1002/cjoc.20030210603
Publication status	Published - Jun 2003
Externally published	Yes

Keywords

Asymmetic catalysis
Bis(oxazoline)
Dibenzo[a, c]cyclo-heptadiene
Diels-Alder reaction

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10.1002/cjoc.20030210603

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title = "Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo[a, c]cycloheptadiene bis(oxazoline) metal complexes",

abstract = "A series of novel chiral C2-symmetric bis (oxazoline) ligands have been synthesized. The copper and magnesium complexes, prepared in situ from copper (II)-triflate or magnesium triflate with the new enantiopure oxazoline ligands, were evaluated as chiral catalysts in the enantioselective Diels-Alder reaction of cyclopentadiene with N-crotenoyl-oxazolidin-2-one. Primary results showed that diastereoselectivity up to 94% and enantioselectivity up to 68% ee for endo products were observed respectively with these ligands.",

keywords = "Asymmetic catalysis, Bis(oxazoline), Dibenzo[a, c]cyclo-heptadiene, Diels-Alder reaction",

author = "Bin Fu and Du, {Da Ming}",

year = "2003",

month = jun,

doi = "10.1002/cjoc.20030210603",

language = "English",

volume = "21",

pages = "597--599",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

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T1 - Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo[a, c]cycloheptadiene bis(oxazoline) metal complexes

AU - Fu, Bin

AU - Du, Da Ming

PY - 2003/6

Y1 - 2003/6

N2 - A series of novel chiral C2-symmetric bis (oxazoline) ligands have been synthesized. The copper and magnesium complexes, prepared in situ from copper (II)-triflate or magnesium triflate with the new enantiopure oxazoline ligands, were evaluated as chiral catalysts in the enantioselective Diels-Alder reaction of cyclopentadiene with N-crotenoyl-oxazolidin-2-one. Primary results showed that diastereoselectivity up to 94% and enantioselectivity up to 68% ee for endo products were observed respectively with these ligands.

AB - A series of novel chiral C2-symmetric bis (oxazoline) ligands have been synthesized. The copper and magnesium complexes, prepared in situ from copper (II)-triflate or magnesium triflate with the new enantiopure oxazoline ligands, were evaluated as chiral catalysts in the enantioselective Diels-Alder reaction of cyclopentadiene with N-crotenoyl-oxazolidin-2-one. Primary results showed that diastereoselectivity up to 94% and enantioselectivity up to 68% ee for endo products were observed respectively with these ligands.

KW - Asymmetic catalysis

KW - Bis(oxazoline)

KW - Dibenzo[a, c]cyclo-heptadiene

KW - Diels-Alder reaction

UR - http://www.scopus.com/inward/record.url?scp=0348083208&partnerID=8YFLogxK

U2 - 10.1002/cjoc.20030210603

DO - 10.1002/cjoc.20030210603

M3 - Article

AN - SCOPUS:0348083208

SN - 1001-604X

VL - 21

SP - 597

EP - 599

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 6

ER -

Asymmetric Diels-Alder reaction catalyzed by novel chiral dibenzo[a, c]cycloheptadiene bis(oxazoline) metal complexes

Abstract

Keywords

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