Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene

Da Ming Du; Bin Fu; Wen Ting Hua

doi:10.1016/S0040-4020(03)00144-3

Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene

Da Ming Du^*, Bin Fu, Wen Ting Hua

^*Corresponding author for this work

Peking University

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

29 Citations (Scopus)

Abstract

A series of chiral C₂-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62%, respectively, for trans- and cis-2-phenylcyclopropanecarboxylate were observed.

Original language	English
Pages (from-to)	1933-1938
Number of pages	6
Journal	Tetrahedron
Volume	59
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(03)00144-3
Publication status	Published - 10 Mar 2003
Externally published	Yes

Keywords

Bis(oxazoline)
Dibenzo[a,c]cycloheptadiene
Enantioselective cyclopropanation
Styrene
Synthesis

Access to Document

10.1016/S0040-4020(03)00144-3

Cite this

@article{2d87854d02834fea8c1f807c04a30657,

title = "Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene",

abstract = "A series of chiral C2-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62\%, respectively, for trans- and cis-2-phenylcyclopropanecarboxylate were observed.",

keywords = "Bis(oxazoline), Dibenzo[a,c]cycloheptadiene, Enantioselective cyclopropanation, Styrene, Synthesis",

author = "Du, \{Da Ming\} and Bin Fu and Hua, \{Wen Ting\}",

year = "2003",

month = mar,

day = "10",

doi = "10.1016/S0040-4020(03)00144-3",

language = "English",

volume = "59",

pages = "1933--1938",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "11",

}

TY - JOUR

T1 - Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene

AU - Du, Da Ming

AU - Fu, Bin

AU - Hua, Wen Ting

PY - 2003/3/10

Y1 - 2003/3/10

N2 - A series of chiral C2-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62%, respectively, for trans- and cis-2-phenylcyclopropanecarboxylate were observed.

AB - A series of chiral C2-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62%, respectively, for trans- and cis-2-phenylcyclopropanecarboxylate were observed.

KW - Bis(oxazoline)

KW - Dibenzo[a,c]cycloheptadiene

KW - Enantioselective cyclopropanation

KW - Styrene

KW - Synthesis

UR - https://www.scopus.com/pages/publications/0037430444

U2 - 10.1016/S0040-4020(03)00144-3

DO - 10.1016/S0040-4020(03)00144-3

M3 - Article

AN - SCOPUS:0037430444

SN - 0040-4020

VL - 59

SP - 1933

EP - 1938

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this