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.

引用

页码：3453 / 3456

页数：4

共 23 条

[21] NEW PALLADIUM-CATALYZED ADDITION OF CYANOTRIMETHYLSILANE TO F-ALKYLATED 1-AZA-1,3-DIENES - A CONVENIENT ROUTE TO BETA, GAMMA-UNSATURATED ALPHA-F-ALKYL-ALPHA-AMINO ACID PRECURSORS
YAMASAKI, Y
MAEKAWA, T
ISHIHARA, T
ANDO, T
CHEMISTRY LETTERS, 1985, (09) : 1387 - 1390
[22] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO-ACID ESTERS - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF METHYL 4-(2-FURYL)-2,7-DIPHENYL-6,8-DIOXO-3,7-DIAZABICYCLO[3.3.0]OCTANE-2-CARBOXYLATE
GRIGG, R
KEMP, J
SHELDRICK, G
TROTTER, J
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (03) : 109 - 111
[23] SEQUENCES OF PROTEINS OF IMMUNOLOGICAL INTEREST - TABULATION AND ANALYSIS OF AMINO-ACID AND NUCLEIC-ACID SEQUENCES OF PRECURSORS, V-REGIONS, C-REGIONS, J-CHAIN, BETA-2-MICROGLOBULINS, MAJOR HISTOCOMPATIBILITY ANTIGENS, THY-1, COMPLEMENT, C-REACTIVE PROTEIN, THYMOPOIETIN, POST-GAMMA GLOBULIN, AND ALPHA-2-MACROGLOBULIN - KABAT,EA, WU,TT, BILOFSKY,H, REIDMILLER,M, PERRY,HTI
PAPPENHEIMER, AM
QUARTERLY REVIEW OF BIOLOGY, 1983, 58 (04): : 553 - 554

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