Tuning Electronic and Steric Effects: Highly Enantioselective [4+1] Pyrroline Annulation of Sulfur Ylides with α,β-Unsaturated Imines

被引：92

作者：

Lu, Liang-Qiu ^{[1
]}

Zhang, Ji-Ji ^{[1
]}

Li, Fang ^{[1
]}

Cheng, Ying ^{[1
]}

An, Jing ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 26期

基金：

美国国家科学基金会;

关键词：

4+1] annulation; nitrogen heterocycles; pyrroline; sulfur; ylides; VINYL SULFONIUM SALTS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION REACTIONS; AMINOSULFOXONIUM SALTS; MIGRATORY CYCLIZATION; CARBONYL-COMPOUNDS; N-SULFONYLIMINES; BOND FORMATION; COMPLEXES;

D O I：

10.1002/anie.201000755

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical equation presented) A change in tune: A novel [4+1] annulation between atropisomeric sulfur ylides 1 and unsaturated imines 2 was developed. The method allows the synthesis of enantioenriched pyrroline products 3 in high yield and with excellent stereocontrol. The origin of stereoinduction was primarily rationalized by a conformational analysis of the ylides. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4495 / 4498

页数：4

共 61 条

[1] Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis [J].

Aggarwal, VK ;

Charmant, JPH ;

Fuentes, D ;

Harvey, JN ;

Hynd, G ;

Ohara, D ;

Picoul, W ;

Robiette, R ;

Vasse, JL ;

Winn, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :2105-2114

[2] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[3] A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities [J].

Aggarwal, VK ;

Alonso, E ;

Bae, I ;

Hynd, G ;

Lydon, KM ;

Palmer, MJ ;

Patel, M ;

Porcelloni, M ;

Richardson, J ;

Stenson, RA ;

Studley, JR ;

Vasse, JL ;

Winn, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10926-10940

[4] Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes [J].

Aggarwal, VK ;

Harvey, JN ;

Richardson, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5747-5756

[5] Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: use of phenyldiazomethane, diazoesters and diazoacetamides [J].

Aggarwal, VK ;

Ferrara, M ;

O'Brien, CJ ;

Thompson, A ;

Jones, RVH ;

Fieldhouse, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1635-1643

[6] [3+2] and [4+1] cycloaddition reactions of Fischer alkoxy(alkenyl)carbene complexes with electronically neutral 1,3-dienes [J].

Barluenga, J ;

López, S ;

Flórez, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (02) :231-+

[7]

Barluenga J., 2003, ANGEW CHEM, V115, P241

[8] Evidence for a concerted [4+1]-cycloaddition between electron-rich carbenes and electron-deficient dienes [J].

Boisvert, Luc ;

Beaumier, Francis ;

Spino, Claude .

ORGANIC LETTERS, 2007, 9 (26) :5361-5363

[9] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[10] Development of a Formal [4+1] Cycloaddition: Pd(OAc)2-Catalyzed Intramolecular Cyclopropanation of 1,3-Dienyl β-Keto Esters and MgI2-Promoted Vinylcyclopropane-Cyclopentene Rearrangement [J].

Coscia, Rockford W. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (07) :2496-+

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