Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions

被引：206

作者：

Klausen, Rebekka S. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

D O I：

10.1021/ol802887h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of one-pot imine formation and asymmetric Pictet-Spengler reactions cocatalyzed by a chiral thiourea and benzoic acid is described. Optically active tetrahydro-beta-carbolines, ubiquitous structural motifs in biologically active natural products, are obtained in high ee directly from tryptamine and aldehyde precursors.

引用

页码：887 / 890

页数：4

共 19 条

[1] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[2] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[3] Mechanistic studies on norcoclaurine synthase of benzylisoquinoline alkaloid biosynthesis: An enzymatic Pictet-Spengler reaction [J].

Luk, Louis Y. P. ;

Bunn, Shannon ;

Liscombe, David K. ;

Facchini, Peter J. ;

Tanner, Martin E. .

BIOCHEMISTRY, 2007, 46 (35) :10153-10161

[4] Strictosidine synthase:: Mechanism of a Pictet-Spengler catalyzing enzyme [J].

Maresh, Justin J. ;

Giddings, Lesley-Ann ;

Friedrich, Anne ;

Loris, Elke A. ;

Panjikar, Santosh ;

Trout, Bernhardt L. ;

Stoeckigt, Joachim ;

Peters, Baron ;

O'Connor, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :710-723

[5]

OSORIO EJ, 2008, ALKALOIDS, V66, P149

[6] Enantioselective pictet-spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding [J].

Raheem, Izzat T. ;

Thiara, Parvinder S. ;

Peterson, Emily A. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (44) :13404-+

[7] Enantioselective thiourea-catalyzed additions to oxocarbenium ions [J].

Reisman, Sarah E. ;

Doyle, Abigail G. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7198-+

[8] Catalytic asymmetric Pictet-Spengler reaction [J].

Seayad, J ;

Seayad, AM ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1086-1087

[9] Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine [J].

Sewgobind, Nishant V. ;

Wanner, Martin J. ;

Ingemann, Steen ;

de Gelder, Rene ;

van Maarseveen, Jan H. ;

Hiemstra, Henk .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) :6405-6408

[10] Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst [J].

Tan, Kian L. ;

Jacobsen, Eric N. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (08) :1315-1317

← 1 2 →