1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition:: A novel approach to α-aryl-β-enamino esters

被引：127

作者：

Jiang, N ^{[1
]}

Qu, ZH ^{[1
]}

Wang, JB ^{[1
]}

机构：

[1] Beijing Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Edu, Dept Chem, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 19期

关键词：

D O I：

10.1021/ol016324p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Tosyl diazoketamines were prepared by addition of the ethyl alpha -diazoacetate anion to N-sulfonylimines. The diazo decomposition of the diazoketamines with Rh-2(OAc)(4) complex resulted in aryl migration to give alpha -aryl-beta -enamino esters in good yields and high stereoselectivity. The effect of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A reaction mechanism involving a "bridged" phenonium ion is proposed.

引用

页码：2989 / 2992

页数：4

共 22 条

[1]

[Anonymous], 1987, MECH THEORY ORGANIC

[2] Stereoselective reduction of enantiopure beta-enamino esters by hydride: A convenient synthesis of both enantiopure beta-amino esters [J].

Cimarelli, C ;

Palmieri, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5557-5563

[3]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[4] ELECTRONIC AND STERIC CONTROL IN CARBON HYDROGEN INSERTION REACTIONS OF DIAZOACETOACETATES CATALYZED BY DIRHODIUM(II) CARBOXYLATES AND CARBOXAMIDES [J].

DOYLE, MP ;

WESTRUM, LJ ;

WOLTHUIS, WNE ;

SEE, MM ;

BOONE, WP ;

BAGHERI, V ;

PEARSON, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :958-964

[5]

FRANZEN V, 1957, LIEBIGS ANN CHEM, V602, P199

[6] SYNTHESIS OF BETA-METHOXY ENONES VIA A NEW 2-CARBON EXTENSION OF CARBOXYLIC-ACIDS [J].

HUDLICKY, T ;

OLIVO, HF ;

NATCHUS, MG ;

UMPIERREZ, EF ;

PANDOLFI, E ;

VOLONTERIO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4767-4770

[7] SHIKIMATE DERIVED METABOLITES .8. CATALYZED INSERTION REACTIONS OF SUBSTITUTED ALPHA-DIAZOESTERS - A NEW SYNTHESIS OF CIS-ENOATES [J].

IKOTA, N ;

TAKAMURA, N ;

YOUNG, SD ;

GANEM, B .

TETRAHEDRON LETTERS, 1981, 22 (42) :4163-4166

[8] Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-beta-KDO. [J].

LopezHerrera, FJ ;

SarabiaGarcia, F .

TETRAHEDRON, 1997, 53 (09) :3325-3346

[9] Indium-mediated organometallic reactions in aqueous media. Stereoselectivity in the crotylation of sulfonimines bearing a proximal chelating group [J].

Lu, WS ;

Chan, TH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3467-3473

[10]

NAGAO K, 1983, SYNTHESIS-STUTTGART, P197

← 1 2 3 →