ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRONES WITH KETENE ACETALS CATALYZED BY CHIRAL OXAZABOROLIDINES

被引：101

作者：

SEERDEN, JPG ^{[1
]}

REIMER, AWASO ^{[1
]}

SCHEEREN, HW ^{[1
]}

机构：

[1] UNIV NIJMEGEN,NSR CTR MOLEC STRUCT DESIGN & SYNTH,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)73373-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymetric 1,3-dipolar cycloaddition of nitrones with ketene acetals is strongly catalyzed by chiral oxazaborolidines derived from N-tosyl-L-alpha-amino acids. The 5,5-dialkoxyisoxazolidines are obtained regioselectively in high yield with high stereoselectivity and moderate enantioselectivity Icp to 62% ee. Mild hydrogenolysis of the N-O bond yields quantitatively the corresponding beta-amino-ester.

引用

页码：4419 / 4422

页数：4

共 37 条

[1] HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS [J].

ABEN, RWM ;

SMIT, R ;

SCHEEREN, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :365-370

[2]

ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253

[3]

BALASUBRAMANIAN N, 1985, ORG PREP P INT, P25

[4] BETA-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS - NEW REAGENTS FOR SYNTHESIS [J].

BARLUENGA, J ;

FANANAS, FJ ;

YUS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4798-4801

[5]

BLACK DSC, 1975, SYNTHESIS-STUTTGART, P205

[6] SYNTHESEVERSUCHE IN DER EMETIN-REIHE .1. 2-OXO-HYDROBENZO[A]CHINOLIZINE [J].

BROSSI, A ;

LINDLAR, H ;

WALTER, M ;

SCHNIDER, O .

HELVETICA CHIMICA ACTA, 1958, 41 (01) :119-139

[7]

Confalone P. N., 1988, ORG REACTIONS, V36, P1

[8] PROTON MAGNETIC-RESONANCE STUDIES OF COMPOUNDS WITH BRIDGEHEAD NITROGEN .33. EFFECT OF A FUSED AROMATIC RING ON CONFORMATIONAL PREFERENCES OF PERHYDROPYRIDO[1,2-C][1,3]OXAZINES AND RELATED COMPOUNDS [J].

CRABB, TA ;

MITCHELL, JS ;

NEWTON, RF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (03) :370-378

[9] ASYMMETRIC BORON-CATALYZED REACTIONS [J].

DELOUX, L ;

SREBNIK, M .

CHEMICAL REVIEWS, 1993, 93 (02) :763-784

[10] NITRONE CYCLOADDITIONS TO 2,3-DIHYDRO-1-PHENYL-1H-PHOSPHOLE 1-OXIDE - DOUBLE ASYMMETRIC INDUCTION AND KINETIC RESOLUTION BY A CHIRAL NITRONE [J].

GOTI, A ;

CICCHI, S ;

BRANDI, A ;

PIETRUSIEWICZ, KM .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1371-1378

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