Chiral C2-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination

Dong Jei Cho; Sang Jin Jeon; Hong Seok Kim; Chan Sik Cho; Sang Chul Shim; Tae Jeong Kim

doi:10.1016/S0957-4166(99)00423-1

Chiral C₂-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination

Dong Jei Cho, Sang Jin Jeon, Hong Seok Kim, Chan Sik Cho, Sang Chul Shim, Tae Jeong Kim

Department of Applied Chemistry

Kyungpook National University

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

86 Scopus citations

Abstract

A new series of chiral C₂-symmetric bisferrocenyldiimine 1 and bisferrocenyldiamines 2 and 3 proved to be efficient ligands for the copper(I)-catalyzed asymmetric cyclopropanation, cyclopropenation, and aziridination of alkenes and alkynes to give high diastereo- and enantioselectivity as well as high chemical yields. In some instances the enantiomeric excesses of cyclopropanated products are among the highest (>97% ee) ever reported. Comparative studies show that stereoselectivity depends highly on the steric variation both in the ligand and the substrate. Other transition metal complexes incorporating some of these ligands such as Ru(3c)Cl₂, [(NBD)Rh(2)]ClO₄, [Cu(2)(MeCN)₂]PF₆, and Pd(2)Cl₂ also demonstrated high enantioselectivity in cyclopropanation reactions.

Original language	English
Pages (from-to)	3833-3848
Number of pages	16
Journal	Tetrahedron Asymmetry
Volume	10
Issue number	19
DOIs	https://doi.org/10.1016/S0957-4166(99)00423-1
State	Published - 24 Sep 1999

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@article{1c78e0a5a6a940fc87fade702904f38f,

title = "Chiral C2-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination",

abstract = "A new series of chiral C2-symmetric bisferrocenyldiimine 1 and bisferrocenyldiamines 2 and 3 proved to be efficient ligands for the copper(I)-catalyzed asymmetric cyclopropanation, cyclopropenation, and aziridination of alkenes and alkynes to give high diastereo- and enantioselectivity as well as high chemical yields. In some instances the enantiomeric excesses of cyclopropanated products are among the highest (>97\% ee) ever reported. Comparative studies show that stereoselectivity depends highly on the steric variation both in the ligand and the substrate. Other transition metal complexes incorporating some of these ligands such as Ru(3c)Cl2, [(NBD)Rh(2)]ClO4, [Cu(2)(MeCN)2]PF6, and Pd(2)Cl2 also demonstrated high enantioselectivity in cyclopropanation reactions.",

author = "Cho, \{Dong Jei\} and Jeon, \{Sang Jin\} and Kim, \{Hong Seok\} and Cho, \{Chan Sik\} and Shim, \{Sang Chul\} and Kim, \{Tae Jeong\}",

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T1 - Chiral C2-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination

AU - Cho, Dong Jei

AU - Jeon, Sang Jin

AU - Kim, Hong Seok

AU - Cho, Chan Sik

AU - Shim, Sang Chul

AU - Kim, Tae Jeong

PY - 1999/9/24

Y1 - 1999/9/24

N2 - A new series of chiral C2-symmetric bisferrocenyldiimine 1 and bisferrocenyldiamines 2 and 3 proved to be efficient ligands for the copper(I)-catalyzed asymmetric cyclopropanation, cyclopropenation, and aziridination of alkenes and alkynes to give high diastereo- and enantioselectivity as well as high chemical yields. In some instances the enantiomeric excesses of cyclopropanated products are among the highest (>97% ee) ever reported. Comparative studies show that stereoselectivity depends highly on the steric variation both in the ligand and the substrate. Other transition metal complexes incorporating some of these ligands such as Ru(3c)Cl2, [(NBD)Rh(2)]ClO4, [Cu(2)(MeCN)2]PF6, and Pd(2)Cl2 also demonstrated high enantioselectivity in cyclopropanation reactions.

AB - A new series of chiral C2-symmetric bisferrocenyldiimine 1 and bisferrocenyldiamines 2 and 3 proved to be efficient ligands for the copper(I)-catalyzed asymmetric cyclopropanation, cyclopropenation, and aziridination of alkenes and alkynes to give high diastereo- and enantioselectivity as well as high chemical yields. In some instances the enantiomeric excesses of cyclopropanated products are among the highest (>97% ee) ever reported. Comparative studies show that stereoselectivity depends highly on the steric variation both in the ligand and the substrate. Other transition metal complexes incorporating some of these ligands such as Ru(3c)Cl2, [(NBD)Rh(2)]ClO4, [Cu(2)(MeCN)2]PF6, and Pd(2)Cl2 also demonstrated high enantioselectivity in cyclopropanation reactions.

UR - https://www.scopus.com/pages/publications/0033405531

U2 - 10.1016/S0957-4166(99)00423-1

DO - 10.1016/S0957-4166(99)00423-1

M3 - Article

AN - SCOPUS:0033405531

SN - 0957-4166

VL - 10

SP - 3833

EP - 3848

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 19

ER -

Chiral C₂-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination

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