The asymmetric hetero-Diels-Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl(2R)-isobornyl glyoxylate

被引:12
作者
Czapla, A
Chajewski, A
Kiegiel, K
Bauer, T
Wielogorski, Z
Urbanczyk-Lipkowska, Z
Jurczak, J
机构
[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
D O I
10.1016/S0957-4166(99)00212-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The recent development of very effective chiral auxiliaries has led to the design of 10-N,N-dicyclohexylsulphamoyl-(R)-isoborneol, which is similar to Oppolzer's (2R)-bornane-10,2-sultam but less effective on account of a less rigid structure. 10-N,N-Dicyclohexylsulphamoyl-(R)-isobornyl glyoxylate was examined in Diels-Alder and organometallic addition reactions. The results obtained were compared with those achieved by application of N-glyoxyloyl-(2R)-bornane-10,2-sultam. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码:2101 / 2111
页数:11
相关论文
共 21 条
[1]   Syntheses of deoxyhexoses from diastereoisomerically pure hetero-Diels-Alder adduct [J].
Bauer, T .
TETRAHEDRON, 1997, 53 (13) :4763-4768
[2]   The stereocontrolled synthesis of methyl 2,6-N,N-diacetyl-D-purpurosaminide C [J].
Bauer, T ;
Jezewski, A ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1405-1412
[3]   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
[4]   Stereochemical course of the [4+2] cycloaddition of 1-methoxybuta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam. The formal synthesis of compactin and mevinolin [J].
Bauer, T ;
Chapuis, C ;
Jezewski, A ;
Kozak, J ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1391-1404
[5]   Highly stereoselective addition of 2-trimethylsilyloxyfuran to N-glyoxyloyl-(2R)-bornane-10,2-sultam [J].
Bauer, T .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :981-984
[6]   Efficient synthesis of N-glyoxyloyl-(2R)-bornane-10,2-sultam [J].
Bauer, T ;
Jezewski, A ;
Chapuis, C ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1385-1390
[7]   MILD LEWIS ACID CATALYSIS - EU(FOD)3-MEDIATED HETERO-DIELS-ALDER REACTION [J].
BEDNARSKI, M ;
DANISHEFSKY, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3716-3717
[8]  
Chapuis C., 1984, THESIS U GENEVA
[9]   The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene [J].
Jezewski, A ;
Chajewska, K ;
Wielogorski, Z ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1741-1749
[10]  
JURCZAK J, 1979, POL J CHEM, V53, P2539