Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates

被引：18

作者：

Doyle, MP ^{[1
]}

Wang, YH ^{[1
]}

Ghorbani, P ^{[1
]}

Bappert, E ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 22期

关键词：

D O I：

10.1021/ol0520121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Two sequential intramolecular carbon-hydrogen insertion or cyclopropa nation reactions of bis-diazoacetates using chiral dirhodium(II) carboxamidate catalysts are reported. The initial metal carbene transformation forms an excess of one enantiomer that with the second transformation further enhances stereocontrol (kinetic amplification). Diastereoselectivity and enantioselectivity for product formation are controlled by the catalyst.

引用

页码：5035 / 5038

页数：4

共 50 条

[41] CHIRAL RUTHENIUM(II)-BIS(2-OXAZOLIN-2-YL) PYRIDINE COMPLEXES - ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS AND DIAZOACETATES
NISHIYAMA, H
ITOH, Y
SUGAWARA, Y
MATSUMOTO, H
AOKI, K
ITOH, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (05) : 1247 - 1262
[42] Mechanistic Insights into Asymmetric C-H Insertion Cooperatively Catalyzed by a Dirhodium(II) Complex and Chiral Phosphoric Acid
Liu, Hui
Duan, Jun-Xin
Qu, Deyu
Guo, Li-Ping
Xie, Zhi-Zhong
ORGANOMETALLICS, 2016, 35 (11) : 2003 - 2009
[43] Chiral Co(II) complex catalyzed asymmetric Michael reactions of β-ketoamides to nitroolefins and alkynones
Zhang, Zuliang
Liu, Xiaohua
Wang, Zhen
Zhao, Xiaohu
Lin, Lili
Feng, Xiaoming
TETRAHEDRON LETTERS, 2014, 55 (28) : 3797 - 3801
[44] ASYMMETRIC HETERO-DIELS-ALDER REACTIONS AND ENE REACTIONS CATALYZED BY CHIRAL COPPER(II) COMPLEXES
JOHANNSEN, M
JORGENSEN, KA
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18): : 5757 - 5762
[45] A new class of chiral Lewis acid catalysts for highly enantioselective hetero-Diels-Alder reactions: Exceptionally high turnover numbers from dirhodium(II) carboxamidates
Doyle, MP
Phillips, IM
Hu, WH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5366 - 5367
[46] Asymmetric Diels-Alder reactions catalyzed by chiral Ni(II)-binaphthyldiimine complexes
Suga, H
Kakehi, A
Mitsuda, M
CHEMISTRY LETTERS, 2002, (09) : 900 - 901
[47] Model intermolecular asymmetric Heck reactions catalyzed by chiral pyridyloxazoline palladium(II) complexes
Dodd, David W.
Toews, Heather E.
Carneiro, Florentino d. S.
Jennings, Michael C.
Jones, Nathan D.
INORGANICA CHIMICA ACTA, 2006, 359 (09) : 2850 - 2858
[48] Asymmetric Induction of Chiral 1,1'-Bis(oxazolinyl)ferrocenes as Ligands in Metal-Catalyzed Cyclopropanation and Diels-Alder Reactions
Zhen QIAO1
Chinese Chemical Letters, 2004, (09) : 1015 - 1018
[49] Asymmetric induction of chiral 1,1′-bis(oxazolinyl)ferrocenes as ligands in metal-catalyzed cyclopropanation and Diels-Alder reactions
Qiao, Z
Shi, XY
Bian, QH
Hou, SC
Wang, M
CHINESE CHEMICAL LETTERS, 2004, 15 (09) : 1015 - 1018
[50] ASYMMETRIC INDUCTION REACTIONS .4. PALLADIUM-CATALYZED ASYMMETRIC ALLYLATIONS OF CHIRAL ENAMINES BEARING PHOSPHINE GROUPS
HIROI, K
ABE, J
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (03) : 616 - 621

← 1 2 3 4 5 →