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

[21] Total synthesis of (S)-(+)-imperanene.: Effective use of regio- and enantioselective intramolecular carbon-hydrogen insertion reactions catalyzed by chiral dirhodium(II) carboxamidates
Doyle, MP
Hu, WH
Valenzuela, MV
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09): : 2954 - 2959
[22] Dirhodium(II) tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]. A new set of effective chiral catalysts for asymmetric intermolecular cyclopropanation reactions with diazoacetates
Doyle, MP
Zhou, QL
Simonsen, SH
Lynch, V
SYNLETT, 1996, (07) : 697 - &
[23] Synthesis of natural lignan lactones via highly enantioselective carbon-hydrogen insertion catalyzed by chiral dirhodium(II) carboxamidates.
Doyle, MP
Protopopova, MN
Zhou, QL
Bode, JW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 322 - ORGN
[24] Design and Synthesis of Novel Chiral Dirhodium(II) Carboxylate Complexes for Asymmetric Cyclopropanation Reactions
Adly, Frady G.
Gardiner, Michael G.
Ghanem, Ashraf
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3447 - 3461
[25] DIASTEREOSELECTIVITY ENHANCEMENT IN CYCLOPROPANATION AND CYCLOPROPENATION REACTIONS OF CHIRAL DIAZOACETATE ESTERS CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXAMIDES
DOYLE, MP
PROTOPOPOVA, MN
BRANDES, BD
DAVIES, HML
HUBY, NJS
WHITESELL, JK
SYNLETT, 1993, (02) : 151 - 153
[26] ASYMMETRIC INTRAMOLECULAR CYCLOPROPANATION WITH ALLYLIC 2-DIAZOPROPANOATES CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXAMIDES
DOYLE, MP
ZHOU, QL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 105 - ORGN
[27] Quaternary Chiral Phthalides Enabled by Dirhodium(II)/Phosphine Catalyzed Asymmetric Carbonyl Addition Cascade
Zhan, Shuming
Xu, Heng
Hong, Biqiong
Gu, Zhenhua
ORGANIC LETTERS, 2024, 26 (38) : 8023 - 8027
[28] ASYMMETRIC-SYNTHESIS OF LACTONES WITH HIGH ENANTIOSELECTIVITY BY INTRAMOLECULAR CARBON HYDROGEN INSERTION REACTIONS OF ALKYL DIAZOACETATES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES
DOYLE, MP
VANOEVEREN, A
WESTRUM, LJ
PROTOPOPOVA, MN
CLAYTON, TW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8982 - 8984
[29] Asymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides
1600, (113):
[30] Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(II) carboxamidates
Watanabe, Yudai
Washio, Takuya
Krishnamurthi, Janagiraman
Anada, Masahiro
Hashimoto, Shunichi
CHEMICAL COMMUNICATIONS, 2012, 48 (55) : 6969 - 6971

← 1 2 3 4 5 →