A peptide-catalyzed asymmetric Stetter reaction

被引：120

作者：

Mennen, SM ^{[1
]}

Blank, JT ^{[1
]}

Tran-Dubé, MB ^{[1
]}

Imbriglio, JE ^{[1
]}

Miller, SJ ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 02期

关键词：

D O I：

10.1039/b414574g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thiazolylalanine, in appropriately functionalized form, has been found to function as an enantioselective catalyst for an intramolecular Stetter reaction. Incorporation of the residue in a number of environments has resulted in a family of catalysts that promote the cyclization of a test substrate with up to 81% enantiomeric excess.

引用

页码：195 / 197

页数：3

共 21 条

[1] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[2] THE THIAZOLIUM CATALYZED BENZOIN CONDENSATION WITH MILD BASE DOES NOT INVOLVE A DIMER INTERMEDIATE [J].

BRESLOW, R ;

KIM, R .

TETRAHEDRON LETTERS, 1994, 35 (05) :699-702

[3] The mechanism of thiazolium catalysis [J].

Breslow, R ;

Schmuck, C .

TETRAHEDRON LETTERS, 1996, 37 (45) :8241-8242

[4] REACTIVITY OF THE THIAZOLIUM C2 YLIDE IN APROTIC-SOLVENTS - NOVEL EXPERIMENTAL-EVIDENCE FOR ADDITION RATHER THAN INSERTION REACTIVITY [J].

CHEN, YT ;

JORDAN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5029-5038

[5] Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope [J].

Copeland, GT ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6496-6502

[6] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[7] Nucleophilic carbenes in asymmetric organocatalysis [J].

Enders, D ;

Balensiefer, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :534-541

[8] Catalytic enantioselective synthesis of sulfinate esters through the dynamic resolution of tert-butanesulfinyl chloride [J].

Evans, JW ;

Fierman, MB ;

Miller, SJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8134-8135

[9] Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles [J].

Guerin, DJ ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2134-2136

[10] Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction [J].

Imbriglio, JE ;

Vasbinder, MM ;

Miller, SJ .

ORGANIC LETTERS, 2003, 5 (20) :3741-3743

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