1,3-dipolar cycloaddition of 1-carboxynitrone: Different stereoselectivity caused by salt effect

被引:22
作者
Tokunaga, Y [1 ]
Ihara, M [1 ]
Fukumoto, K [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1016/0040-4039(96)01336-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatments of 1-carboxynitrone 1 with monosabstituted olefins 2 caused a 1,3-dipolar cycloadditions to give cis-isoxazolidines 3 with high stereoselection. On the other hand, reactions of 1 with olefins in the presence of triethylamine afforded trans-isomers 4 predominantly. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6157 / 6160
页数:4
相关论文
共 23 条
[1]  
AGAMI C, 1992, SYNLETT, P847
[2]   ALPHA-OXIMINO AMIDE TRIANIONS IN THE STEREOSELECTIVE SYNTHESIS OF ISOXAZOLINES AND GAMMA-HYDROXY-ALPHA-AMINO ACIDS [J].
BARRETT, AGM ;
DHANAK, D ;
LEBOLD, SA ;
RUSSELL, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1894-1901
[3]   APPLICATIONS OF CROTYLDIISOPINOCAMPHEYLBORANES IN SYNTHESIS - THE TOTAL SYNTHESIS OF NIKKOMYCIN-B [J].
BARRETT, AGM ;
LEBOLD, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4875-4884
[4]   AN ASYMMETRIC-SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID FROM D-SERINE [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :2979-2984
[5]   ENDO-SELECTIVE REACTIONS OF ALPHA,BETA-UNSATURATED HEXACARBONYLDIIRON BRIDGING ACYL COMPLEXES WITH NITRONES [J].
GILBERTSON, SR ;
DAWSON, DP ;
LOPEZ, OD ;
MARSHALL, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4431-4432
[6]  
GULL R, 1985, SYNTHESIS-STUTTGART, P1052
[7]   A SHORT-STEP SYNTHESIS OF 4-HYDROXYPROLINE [J].
HARA, J ;
INOUYE, Y ;
KAKISAWA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (12) :3871-3872
[8]   STEREOSELECTIVE SYNTHESIS OF (+/-)-ERYTHRO- AND THREO-GAMMA-HYDROXYNORVALINE [J].
HARDING, KE ;
MARMAN, TH ;
NAM, DH .
TETRAHEDRON LETTERS, 1988, 29 (14) :1627-1630
[9]   SCYTONEMIN-A, A NOVEL CALCIUM-ANTAGONIST FROM A BLUE-GREEN-ALGA [J].
HELMS, GL ;
MOORE, RE ;
NIEMCZURA, WP ;
PATTERSON, GML ;
TOMER, KB ;
GROSS, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1298-1307
[10]   POLYOXINS - PYRIMIDINE NUCLEOSIDE PEPTIDE ANTIBIOTICS INHIBITING FUNGAL CELL-WALL BIOSYNTHESIS [J].
ISONO, K ;
SUZUKI, S .
HETEROCYCLES, 1979, 13 :333-351