Efficient synthesis of N-glyoxyloyl-(2R)-bornane-10,2-sultam

被引:28
作者
Bauer, T
Jezewski, A
Chapuis, C
Jurczak, J
机构
[1] UNIV WARSAW,DEPT CHEM,PL-02093 WARSAW,POLAND
[2] POLISH ACAD SCI,INST ORGAN CHEM,PL-01224 WARSAW,POLAND
[3] FIRMENICH CO,RES LABS,CH-2111 GENEVA 8,SWITZERLAND
关键词
D O I
10.1016/0957-4166(96)00155-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Starting from (2R)-bornane-10,2-sultam 1, the useful chiron N-glyoxyloyl-(2R)-bornane-10,2-sultam 5 is prepared via its crystalline precursor 4. The hemiacetal 4 whose structure was proved by the X-ray analysis is formed in diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1385 / 1390
页数:6
相关论文
共 25 条
[1]   PARTIAL ASYMMETRIC INDUCTION IN ENE REACTION [J].
ACHMATOWICZ, O ;
SZECHNER, B .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :964-+
[2]   ASYMMETRIC DIELS-ALDER REACTION OF 1-METHOXYBUTA-1,3-DIENE WITH (2R)-N-GLYOXYLOYLBORNANE-10,2-SULTAM [J].
BAUER, T ;
CHAPUIS, C ;
KOZAK, J ;
JURCZAK, J .
HELVETICA CHIMICA ACTA, 1989, 72 (03) :482-486
[3]   DIASTEREOSELECTIVE SYNTHESIS OF THE LACTONE PORTION OF COMPACTIN AND MEVINOLIN [J].
BAUER, T ;
KOZAK, J ;
CHAPUIS, C ;
JURCZAK, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) :1178-1179
[4]  
BAUER T, 1990, HELV CHIM ACTA, P1178
[5]   SYNTHESIS OF OPTICALLY-ACTIVE 4-HYDROXYMANDELIC ACID AND DERIVATIVES VIA REGIOSELECTIVE AND STEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION [J].
BIGI, F ;
SARTORI, G ;
MAGGI, R ;
CANTARELLI, E ;
GALAVERNA, G .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2411-2414
[6]   ASYMMETRIC REACTIONS .64. ENANTIOSELECTIVE DIELS-ALDER REACTION OF (E)-1-TRIMETHYL-SILYLOXY-1,3-BUTADIENE WITH CHIRAL GLYOXYLATES [J].
CERVINKA, O ;
SVATOS, A ;
TRSKA, P ;
PECH, P .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (01) :230-244
[7]   SYNTHESIS OF 3,6-DIAMINO-2,3,4,6-TETRADEOXY-DL-THREO-HEXOPYRANOSE DERIVATIVES, SUBSTRATES FOR SYNTHESIS OF NEGAMYCIN [J].
CHMIELEWSKI, M ;
JURCZAK, J ;
ZAMOJSKI, A .
TETRAHEDRON, 1978, 34 (19) :2977-2981
[8]   GENERAL-APPROACH TO THE SYNTHESIS OF NATURALLY-OCCURRING DELTA-LACTONES [J].
CHMIELEWSKI, M ;
JURCZAK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2230-2233
[9]   CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].
DUTHALER, RO ;
HAFNER, A .
CHEMICAL REVIEWS, 1992, 92 (05) :807-832
[10]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881