共 14 条
A new strategy for the elaboration of pyrrolidine N-oxides using the reverse-Cope elimination
被引:14
作者:

Hanrahan, JR
论文数: 0 引用数: 0
h-index: 0
机构:
Cardiff Univ, Dept Chem, Cardiff CF1 3TB, S Glam, Wales Cardiff Univ, Dept Chem, Cardiff CF1 3TB, S Glam, Wales

Knight, DW
论文数: 0 引用数: 0
h-index: 0
机构:
Cardiff Univ, Dept Chem, Cardiff CF1 3TB, S Glam, Wales Cardiff Univ, Dept Chem, Cardiff CF1 3TB, S Glam, Wales
机构:
[1] Cardiff Univ, Dept Chem, Cardiff CF1 3TB, S Glam, Wales
关键词:
D O I:
10.1039/a806335d
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Condensations of the unsaturated nitrones 13 with lithiated methyl phenyl sulfone provide excellent yields of the unsaturated hydroxylamines 14 as single stereoisomers, which undergo rapid reverse-Cope elimination at ambient temperature, assisted by the constraint of the acetonide ring, leading to the pyrrolidine N-oxides 15 as single enantiomers.
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页码:2231 / 2232
页数:2
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- [1] Factors influencing the reverse-Cope approach to 1,2,5-oxadiazinanes from allylamines and nitrones: Optimization of a new vicinal diamine synthesis[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8545 - 8548Bell, KE论文数: 0 引用数: 0 h-index: 0机构: UNIV NOTTINGHAM, DEPT CHEM, NOTTINGHAM NG7 2RD, ENGLANDCoogan, MP论文数: 0 引用数: 0 h-index: 0机构: UNIV NOTTINGHAM, DEPT CHEM, NOTTINGHAM NG7 2RD, ENGLANDGravestock, MB论文数: 0 引用数: 0 h-index: 0机构: UNIV NOTTINGHAM, DEPT CHEM, NOTTINGHAM NG7 2RD, ENGLANDKnight, DW论文数: 0 引用数: 0 h-index: 0机构: UNIV NOTTINGHAM, DEPT CHEM, NOTTINGHAM NG7 2RD, ENGLANDThornton, SR论文数: 0 引用数: 0 h-index: 0机构: UNIV NOTTINGHAM, DEPT CHEM, NOTTINGHAM NG7 2RD, ENGLAND
- [2] NITRONES AND OXAZIRIDINES .22. PREPARATION AND CYCLIZATION OF SOME DELTA,EPSILON-UNSATURATED HYDROXYLAMINES[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) : 2317 - 2322BLACK, DSC论文数: 0 引用数: 0 h-index: 0DOYLE, JE论文数: 0 引用数: 0 h-index: 0
- [3] REVERSE COPE ELIMINATION-REACTIONS .2. APPLICATION TO SYNTHESIS(1)[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) : 5803 - 5807CIGANEK, E论文数: 0 引用数: 0 h-index: 0机构: Kennett Square, PA 19348
- [4] Reverse-Cope cyclisations of thiahydroxylamines derived from the addition of allylic thiols to nitrones: Syntheses of 1,3-thiazolidine-N-oxides and 1,5,2-oxathiazinanes[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8549 - 8552Coogan, MP论文数: 0 引用数: 0 h-index: 0机构: ZENECA PHARMACEUT,MACCLESFIELD SK10 4TJ,CHESHIRE,ENGLANDGravestock, MB论文数: 0 引用数: 0 h-index: 0机构: ZENECA PHARMACEUT,MACCLESFIELD SK10 4TJ,CHESHIRE,ENGLANDKnight, DW论文数: 0 引用数: 0 h-index: 0机构: ZENECA PHARMACEUT,MACCLESFIELD SK10 4TJ,CHESHIRE,ENGLANDThornton, SR论文数: 0 引用数: 0 h-index: 0机构: ZENECA PHARMACEUT,MACCLESFIELD SK10 4TJ,CHESHIRE,ENGLAND
- [5] N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines .8. the scope of tandem reactions involving hydroxylamine-alkyne cyclisations[J]. TETRAHEDRON, 1996, 52 (35) : 11601 - 11624Davison, EC论文数: 0 引用数: 0 h-index: 0机构: UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLANDForbes, IT论文数: 0 引用数: 0 h-index: 0机构: UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLANDHolmes, AB论文数: 0 引用数: 0 h-index: 0机构: UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLANDWarner, JA论文数: 0 引用数: 0 h-index: 0机构: UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
- [6] Stereoselective addition of 2-furyllithium and 2-thiazolyllithium to sugar nitrones. Synthesis of carbon-linked glycoglycines[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) : 5484 - 5496Dondoni, A论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALYJunquera, F论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALYMerchan, FL论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALYMerino, P论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALYScherrmann, MC论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALYTejero, T论文数: 0 引用数: 0 h-index: 0机构: UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALY
- [7] STEREOSELECTIVE AMINOHOMOLOGATION OF CHIRAL ALPHA-ALKOXY ALDEHYDES VIA THIAZOLE ADDITION TO NITRONES - APPLICATION TO THE SYNTHESIS OF N-ACETYL-D-MANNOSAMINE[J]. TETRAHEDRON LETTERS, 1992, 33 (29) : 4221 - 4224DONDONI, A论文数: 0 引用数: 0 h-index: 0机构: UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAINJUNQUERA, F论文数: 0 引用数: 0 h-index: 0机构: UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAINMERCHAN, FL论文数: 0 引用数: 0 h-index: 0机构: UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAINMERINO, P论文数: 0 引用数: 0 h-index: 0机构: UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAINTEJERO, T论文数: 0 引用数: 0 h-index: 0机构: UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN
- [8] Cycloaddition reactions for the synthesis of piperidine and indolizidine alkaloids[J]. PURE AND APPLIED CHEMISTRY, 1997, 69 (03) : 531 - 536Holmes, AB论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadBourdin, B论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadCollins, I论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadDavison, EC论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadRudge, AJ论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadStork, TC论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield RoadWarner, JA论文数: 0 引用数: 0 h-index: 0机构: University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road
- [9] CYCLIZATION OF UNSATURATED HYDROXYLAMINE DERIVATIVES[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) : 855 - 863HOUSE, HO论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332MANNING, DT论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332MELILLO, DG论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332LEE, LF论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332HAYNES, OR论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332WILKES, BE论文数: 0 引用数: 0 h-index: 0机构: GEORGIA INST TECHNOL,SCH CHEM,ATLANTA,GA 30332
- [10] Quantum chemical reaction path and transition state for a model cope (and reverse cope) elimination[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (19) : 3554 - 3560Komaromi, I论文数: 0 引用数: 0 h-index: 0机构: SCIENCES II, CH-1211 GENEVA 4, SWITZERLAND SCIENCES II, CH-1211 GENEVA 4, SWITZERLANDTronchet, JMJ论文数: 0 引用数: 0 h-index: 0机构: SCIENCES II, CH-1211 GENEVA 4, SWITZERLAND SCIENCES II, CH-1211 GENEVA 4, SWITZERLAND