Cycloaddition reactions of carbohydrate derivatives.: Part 7.: [3+2] cycloadditions of chiral nitrilimines

被引:12
作者
Agócs, A
Bényei, A
Somogyi, L
Herczegh, P
机构
[1] Lajos Kossuth Univ, Hungarian Acad Sci, Antibiot Res Grp, H-4010 Debrecen, Hungary
[2] Lajos Kossuth Univ, Dept Phys Chem, H-4010 Debrecen, Hungary
基金
匈牙利科学研究基金会;
关键词
D O I
10.1016/S0957-4166(98)00356-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The diastereoserective 1,3-dipolar cycloaddition reactions of chiral alkenes with a nitrilimine derived from D-galactose phenylhydrazone were studied. The best stereoselectivity was observed with N-acryloyl-(-)-camphor sultam 9, as the chiral inductor, to produce compound 8. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3359 / 3363
页数:5
相关论文
共 13 条
[1]  
ARAMELLA P, 1984, 1 3 DIPOLAR CYCLOADD, P291
[2]   First highly regio- and diastereoselective synthesis of Δ2-pyrazolines by [3+2] cycloaddition of chiral non-racemic Fischer carbene complexes with nitrilimines [J].
Barluenga, J ;
Fernández-Marí, F ;
Aguilar, E ;
Viado, AL ;
Olano, B .
TETRAHEDRON LETTERS, 1998, 39 (27) :4887-4890
[3]   A 2-STEP SYNTHESIS OF CAMPHOSULTAM [J].
CAPET, M ;
DAVID, F ;
BERTIN, L ;
HARDY, JC .
SYNTHETIC COMMUNICATIONS, 1995, 25 (21) :3323-3327
[4]   NEW AND HIGHLY EFFECTIVE METHOD FOR OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS TO CARBONYL-COMPOUNDS [J].
COREY, EJ ;
KIM, CU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7586-&
[5]   Nitrilimines: Evidence for the allenic structure in solution, experimental and ab initio studies of the barrier to racemization, and first diastereoselective [3+2]-cycloaddition [J].
Faure, JL ;
Reau, R ;
Wong, MW ;
Koch, R ;
Wentrup, C ;
Bertrand, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2819-2824
[6]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[7]   CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .6. QUINOLIZIDINE ANALOGS OF CASTANOSPERMINE [J].
HERCZEGH, P ;
KOVACS, I ;
SZILAGYI, L ;
SZTARICSKAI, F ;
BERECIBAR, A ;
RICHE, C ;
CHIARONI, A ;
OLESKER, A ;
LUKACS, G .
TETRAHEDRON, 1995, 51 (10) :2969-2978
[8]   THE FORMATION OF NITRILE IMINES IN THE THERMAL BREAKDOWN OF 2,5-DISUBSTITUTED TETRAZOLES [J].
HUISGEN, R ;
SEIDEL, M ;
SAUER, J ;
MCFARLAND, JW ;
WALLBILLICH, G .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (06) :892-893
[9]  
KIM BH, 1993, TETRAHEDRON, V49, P293
[10]   Enantioselective preparation of 2',3'-dideoxynucleosides and their analogues from ring-expansion of cyclobutanones .2. Synthesis of 2',3'-dideoxyribosides and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane [J].
LeeRuff, E ;
Xi, FD ;
Qie, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1547-1550