Enantio- and diastereoselective synthesis of isoxazolidines by asymmetric 1,3-dipolar cycloaddition of nitrones

被引:47
作者
Ukaji, Y
Taniguchi, K
Sada, K
Inomata, K
机构
[1] Department of Chemistry, Faculty of Science, Kanazawa University, Kakuma, Kanazawa
关键词
D O I
10.1246/cl.1997.547
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric 1,3-dipolar cycloaddition of nitrones possessing electron withdrawing group to an achiral allyl alcohol was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo- and enantioselectivity.
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页码:547 / 548
页数:2
相关论文
共 17 条
[1]   TOWARDS A NEW TYPE OF HMG-COA REDUCTASE INHIBITOR [J].
BARTH, M ;
BELLAMY, FD ;
RENAUT, P ;
SAMRETH, S ;
SCHUBER, F .
TETRAHEDRON, 1990, 46 (19) :6731-6740
[2]  
BOERSMA J, 1966, TETRAHEDRON LETT, P1521
[3]   RELATIVE REACTIVITIES OF NORMAL AND ANGLE STRAINED CYCLO-OLEFINS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS - ROTATIONAL BARRIERS IN NITRONES [J].
BOYLE, LL ;
PEAGRAM, MJ ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (09) :1728-&
[4]  
Curran D. P., 1988, ADV CYCLOADDITION, V1-6
[5]  
CURRAN DP, 1990, ADV CYCLOADDITION, V2
[6]   Control of diastereo- and enantioselectivity in metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrones with alkenes. Experimental and theoretical investigations [J].
Gothelf, KV ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :346-355
[7]   A highly diastereoselective and enantioselective Ti(OTos)(2)-TADDOLate-catalyzed 1,3-dipolar cycloaddition reaction of alkenes with nitrones [J].
Gothelf, KV ;
Thomsen, I ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) :59-64
[8]   Palladium-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to olefins [J].
Hori, K ;
Kodama, H ;
Ohta, T ;
Furukawa, I .
TETRAHEDRON LETTERS, 1996, 37 (33) :5947-5950
[9]   1,3-DIPOLAR CYCLOADDITIONS .50. PROPERTIES OF UNSATURATED COMPOUNDS AS ACYL NITRONE ADDUCTS [J].
HUISGEN, R ;
HAUCK, H ;
SEIDL, H ;
BURGER, M .
CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (04) :1117-&
[10]   NOVEL E-Z EQUILIBRIUM OF "N-ALKYL-ALPHA-ALKOXYCARBONYLNITRONE IN SOLUTION [J].
INOUYE, Y ;
HARA, J ;
KAKISAWA, H .
CHEMISTRY LETTERS, 1980, (11) :1407-1410