STEREOCHEMISTRY OF THE CATALYZED DIELS-ALDER REACTION BETWEEN CYCLOPENTADIENE AND DIMETHYL MONOTHIONOFUMARATE - SOFT VERSUS HARD LEWIS-ACIDS

被引：12

作者：

BRADDOCK, DC

BROWN, JM

GUIRY, PJ

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 16期

关键词：

D O I：

10.1039/c39930001244

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the title reaction, hard Lewis acids promote the formation of the endo-ester diastereoisomer with up to 96% selectivity whereas soft Lewis acids give the endo-thionoester with up to 89% selectivity. BF3.OEt2 behaves as if it were in the latter category, giving 94% endo-thionoester.

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页码：1244 / 1246

页数：3

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共 31 条

[1] THE COPPER CATALYZED REACTION OF SODIUM METHOXIDE WITH ARYL BROMIDES - A MECHANISTIC STUDY LEADING TO A FACILE SYNTHESIS OF ANISOLE DERIVATIVES [J].

AALTEN, HL ;

VANKOTEN, G ;

GROVE, DM ;

KUILMAN, T ;

PIEKSTRA, OG ;

HULSHOF, LA ;

SHELDON, RA .

TETRAHEDRON, 1989, 45 (17) :5565-5578

[2]

ALPER H, 1979, J AM CHEM SOC, V91, P6582

[3]

BADOVSKAYA LA, 1979, J ORG CHEM USSR, V15, P43

[4] DIASTEREOSELECTIVE DIELS-ALDER REACTIONS OF OPTICALLY-ACTIVE VINYL SULFOXIDES [J].

BRIMBLE, MA ;

DAVIS, BR .

TETRAHEDRON, 1985, 41 (21) :4965-4972

[5] HYDROBORATION .88. BORANE-1,4-THIOXANE - A NEW, CONVENIENT HYDROBORATING AGENT FOR THE PREPARATION OF REPRESENTATIVE BORANE REAGENTS [J].

BROWN, HC ;

MANDAL, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4970-4976

[6] STEPWISE REACTION OF CS2 WITH THE NICKELACYCLOPENTENE COMPLEXES (R3P)2NI(CH2CME2-O-C6H4) - INFLUENCE OF THE ANCILLARY PHOSPHINE-LIGANDS [J].

CAMPORA, J ;

CARMONA, E ;

GUTIERREZPUEBLA, E ;

POVEDA, ML ;

RUIZ, C .

ORGANOMETALLICS, 1988, 7 (12) :2577-2579

[7] THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].

CHILDS, RF ;

MULHOLLAND, DL ;

NIXON, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808

[8] GEOMETRICAL ASPECTS OF THE ACTIVATION OF KETONES BY LEWIS-ACIDS [J].

CORCORAN, RC ;

MA, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4536-4542

[9] 1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].

COREY, EJ ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967

[10] TOTAL SYNTHESIS OF GIBBERELLIC-ACID - A SIMPLE SYNTHESIS OF A KEY INTERMEDIATE [J].

COREY, EJ ;

MUNROE, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6129-6130

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