INFLUENCE OF N-PROTECTING GROUPS ON THE STEREOCHEMICAL COURSE OF [4+2] CYCLOADDITION OF ACTIVATED DIENES TO ALPHA-AMINO ALDEHYDES

被引:17
作者
GOLEBIOWSKI, A
RACZKO, J
JACOBSSON, U
JURCZAK, J
机构
[1] POLISH ACAD SCI,INST ORGAN CHEM,PL-01224 WARSAW,POLAND
[2] ROYAL INST TECHNOL,DEPT ORGAN CHEM,S-10044 STOCKHOLM 70,SWEDEN
关键词
D O I
10.1016/S0040-4020(01)80943-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereochemical aspects of high-pressure [4+2] cycloaddition between 1-methoxybuta-1,3-diene and N-protected alpha-amino aldehydes are discussed. In addition, the zinc bromide catalyzed cyclocondensation of 1-ethoxy-3-silyloxybuta-1,3-diene and N-protected alpha-amino aldehydes is studied, at ambient pressure.
引用
收藏
页码:1053 / 1064
页数:12
相关论文
共 30 条
[1]   CHEMISTRY OF ELECTRON-RICH CONJUGATED POLYENES .4. SIMPLE AND GENERAL-SYNTHESIS OF 1-ALKOXY-3-TRIMETHYLSILYLOXYBUTA-1,3-DIENES [J].
ABEN, RW ;
SCHEEREN, HW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3132-3138
[2]   SOME DERIVATIVES OF OPTICALLY ACTIVE ALPHA-AMINO ALDEHYDES - AMINO ACIDS .10. [J].
BALENOVIC, K ;
BREGANT, N ;
CERAR, D ;
FLES, D ;
JAMBRESIC, I .
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (03) :297-302
[3]   CRAM RULE SELECTIVITY IN THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF CHIRAL ALDEHYDES - A CONVENIENT ROUTE TO CHIRAL SYSTEMS OF BIOLOGICAL INTEREST [J].
DANISHEFSKY, S ;
KOBAYASHI, S ;
KERWIN, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1981-1983
[4]   USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[5]   UNSATURATED CARBOHYDRATES .2. 3 REACTIONS LEADING TO UNSATURATED GLYCOPYRANOSIDES [J].
FERRIER, RJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC) :5443-&
[6]   STEREODIVERGENT SYNTHESES OF THREO-6-AMINO-6-DEOXYHEPTOSULOSE AND ERYTHRO-6-AMINO-6-DEOXYHEPTOSULOSE DERIVATIVES VIA AN OPTICALLY-ACTIVE OXAZOLIDINE ALDEHYDE [J].
GARNER, P ;
RAMAKANTH, S .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2609-2612
[7]   TOTAL SYNTHESIS OF D,L-PURPUROSAMINE-C [J].
GOLEBIOWSKI, A ;
JACOBSSON, U ;
CHMIELEWSKI, M ;
JURCZAK, J .
TETRAHEDRON, 1987, 43 (03) :599-605
[8]   THE TOTAL SYNTHESIS OF DESTOMIC ACID [J].
GOLEBIOWSKI, A ;
JURCZAK, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (04) :263-264
[9]  
GOLEBIOWSKI A, 1986, HETEROCYCLES, V24, P1205
[10]   TOTAL SYNTHESIS OF PURPUROSAMINE-B FROM D-ALANINE [J].
GOLEBIOWSKI, A ;
JACOBSSON, U ;
RACZKO, J ;
JURCZAK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3759-3760