Organocatalytic Asymmetric Desymmetrization-Fragmentation of Cyclic Ketones

被引：70

作者：

Dickmeiss, Gustav ^{[1
]}

De Sio, Vincenzo ^{[1
]}

Udmark, Jonas ^{[1
]}

Poulsen, Thomas B. ^{[1
]}

Marcos, Vanesa ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Danish Natl Res Fdn, Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 36期

基金：

新加坡国家研究基金会;

关键词：

asymmetric catalysis; cinchona alkaloids; desymmetrization; fragmentation; thiourea functionality; N-TERT-BUTANESULFINYL; ENANTIOSELECTIVE SYNTHESIS; ALKENYLBORONIC ACIDS; CONJUGATE ADDITION; ARYLBORONIC ACIDS; NITROALKENES; PROSTAGLANDINS; THIOLS; DERIVATIVES; ANHYDRIDES;

D O I：

10.1002/anie.200903253

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ticket to total synthesis: The title reaction of meso cyclopropane cyclopentanones and epoxycyclopentanones was catalyzed by thiourea-containing cinchona alkaloids with good to excellent enantioselectivity (see scheme). The concept was extended to a one-pot asymmetric desymmetrization-fragmentation- Michael addition by including a nucleophile. A kinetic resolution based on this method was also demonstrated. © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.

引用

页码：6650 / 6653

页数：4

共 54 条

[1] Asymmetric 1,4-Addition of Oxazolones to Nitroalkenes by Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: Synthesis of α,α-Disubstituted α-Amino Acids [J].

Aleman, Jose ;

Milelli, Andrea ;

Cabrera, Silvia ;

Reyes, Efraim ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :10958-10966

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[4]

[Anonymous], 2008, ANGEW CHEM

[5] AN ASYMMETRIC-SYNTHESIS OF CIS-4-TERT-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS [J].

ASAMI, M .

TETRAHEDRON LETTERS, 1985, 26 (47) :5803-5806

[6] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters [J].

Beenen, Melissa A. ;

Weix, Daniel J. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6304-6305

[7]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[8] Enantioselective aza-Henry reaction using cinchona organocatalysts [J].

Bernardi, L ;

Fini, F ;

Herrera, RP ;

Ricci, A ;

Sgarzani, V .

TETRAHEDRON, 2006, 62 (2-3) :375-380

[9] Novel preparation of (-)-4-hydroxycyclohex-2-enone: reaction of 4-hydroxycyclohex-2-enone and 4-hydroxycyclopent-2-enone with some thiols [J].

Bickley, JF ;

Evans, P ;

Meek, A ;

Morgan, BS ;

Roberts, SM .

TETRAHEDRON-ASYMMETRY, 2006, 17 (03) :355-362

[10] One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers [J].

Chae, JH ;

Yun, JS ;

Buchwald, SL .

ORGANIC LETTERS, 2004, 6 (26) :4809-4812

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