CYCLOADDITION REACTIONS OF GAMMA-AMINO ALPHA,BETA-DIDEHYDRO AMINO-ACID ESTERS - A TEST CASE FOR THE PRINCIPLE OF 1,3-ALLYLIC STRAIN

被引：41

作者：

REETZ, MT ^{[1
]}

KAYSER, F ^{[1
]}

HARMS, K ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,W-3550 MARBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)92661-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Dibenzylainino aldehydes, readily accessible from amino acids, can be converted into gamma-N,N-dibenzylamino alpha,beta-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain.

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页码：3453 / 3456

页数：4

相关论文

共 32 条

[1]

[Anonymous], 1991, ANGEW CHEM, V103, P1559

[2]

[Anonymous], 1985, ASYMMETRIC SYNTHESIS

[3] STEALTH STEREOCONTROL - STEREOCHEMICAL REVERSAL OF A MICHAEL ADDITION-REACTION [J].

BARRETT, AGM ;

WEIPERT, PD ;

DHANAK, D ;

HUSA, RK ;

LEBOLD, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9820-9824

[4] 1,4-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BEARING A GAMMA-STEREOCENTER - A MOLECULAR MECHANICS MODEL FOR STERIC INTERACTIONS IN THE TRANSITION-STATE [J].

BERNARDI, A ;

CAPELLI, AM ;

GENNARI, C ;

SCOLASTICO, C .

TETRAHEDRON-ASYMMETRY, 1990, 1 (01) :21-32

[5] CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD [J].

BROEKER, JL ;

HOFFMANN, RW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5006-5017

[6] DIRECTED HOMOGENEOUS HYDROGENATION [J].

BROWN, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (03) :190-203

[7] ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9858-9859

[8] ACTION OF DIAZOMETHANE ON METHYL (Z(OR E))-2-(ACYLAMINO)CINNAMATES - A NEW ROUTE TO METHYL (Z)-2-(ACYLAMINO)-3-METHYLCINNAMATES [J].

CATIVIELA, C ;

DEVILLEGAS, MDD ;

MAYORAL, JA ;

MELENDEZ, E .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3167-3169

[9] STEREOSELECTIVITY OF THE NUCLEOPHILIC-ADDITION OF ORGANOCOPPER REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - ABINITIO MOLECULAR-ORBITAL STUDIES OF STERIC AND ELECTRONIC EFFECTS [J].

DORIGO, AE ;

MOROKUMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6524-6536

[10] CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS [J].

GARBISCH, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5561-+

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