Ammonia-promoted fragmentation of 2-alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones

被引：5

作者：

Dai, MS ^{[1
]}

Zhang, XQ ^{[1
]}

Khim, SK ^{[1
]}

Schultz, AG ^{[1
]}

机构：

[1] Rensselaer Polytech Inst, Dept Chem, Troy, NY 12180 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 01期

关键词：

D O I：

10.1021/jo048408s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo ammonia-promoted fragmentation reactions to provide butenolides, gamma-butyrolactone, and/or, beta,gamma-epoxycyclohexanones. Product distribution is governed by the relative size of the substituents at C-2 and C-4 of the cyclohexanones. Butenolide amide, the major product from the fragmentation, is further converted into their respective piperidinone and pyrrolidine derivatives.

引用

页码：384 / 387

页数：4

共 25 条

[1] AHN KH, 1994, TETRAHEDRON LETT, V35, P1875
[2] CATALYSIS OF THE SPECIFIC MICHAEL ADDITION - THE EXAMPLE OF ACRYLATE ACCEPTORS
CABRAL, J
LASZLO, P
MAHE, L
MONTAUFIER, MT
RANDRIAMAHEFA, SL
[J]. TETRAHEDRON LETTERS, 1989, 30 (30) : 3969 - 3972
[3] 1,4-ADDITION REACTIONS TO ALPHA,BETA-UNSATURATED TERTIARY AMIDES
CHUIT, C
CORRIU, RJP
REYE, C
[J]. TETRAHEDRON LETTERS, 1982, 23 (52) : 5531 - 5534
[4] MICHAEL REACTIONS ON UNSATURATED ALPHA-AMIDES AND BETA-AMIDES ACTIVATED BY THE CSF-SI(OCH3)4 SYSTEM
CHUIT, C
CORRIU, RJP
PERZ, R
REYE, C
[J]. TETRAHEDRON, 1986, 42 (08) : 2293 - 2301
[5] (4S,5S)-4-BENZYLAMINO-5-[((TERT-BUTYL)DIPHENYLSILYL)OXYMETHYL]-DIHYDRO-2(3H)-FURANONE - A NEW INTERMEDIATE FOR THE ENANTIOSPECIFIC SYNTHESIS OF BETA-AMINOESTERS AND BETA-LACTAMS
COLLIS, MP
HOCKLESS, DCR
PERLMUTTER, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (39) : 7133 - 7136
[6] BAKERS-YEAST REDUCTIONS OF BETA-OXOPYRROLIDINECARBOXYLATES - SYNTHESIS OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-GEISSMAN-WAISS LACTONE, A USEFUL PRECURSOR TO PYRROLIZIDINE ALKALOIDS
COOPER, J
GALLAGHER, PT
KNIGHT, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12): : 1313 - 1317
[7] 1,4-ADDITION REACTIONS TO METHACRYLAMIDE - A ONE POT SYNTHESIS OF 3,4-DIHYDRO 2(1H)-PYRIDINONES AND 3,5-DISUBSTITUTED GLUTARIMIDES
CORRIU, RJP
PERZ, R
[J]. TETRAHEDRON LETTERS, 1985, 26 (10) : 1311 - 1314
[8] [2+2] CYCLOADDITION REACTION OF CYCLIC ENECARBAMATES AND ENAMIDES WITH KETENES - A SHORT AND EFFICIENT SYNTHESIS OF THE GEISSMAN-WAISS LACTONE
DEFARIA, AR
MATOS, CRR
CORREIA, CRD
[J]. TETRAHEDRON LETTERS, 1993, 34 (01) : 27 - 30
[9] ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION DETERMINATION OF BETA-AMINO-GAMMA-BUTYROLACTONES AND AMINO DIOLS
DELANGE, B
VANBOLHUIS, F
FERINGA, BL
[J]. TETRAHEDRON, 1989, 45 (21) : 6799 - 6818
[10] THE AZA-ROBINSON ANNULATION - AN APPLICATION TO THE SYNTHESIS OF ISO-A58365A
FANG, FG
PRATO, M
KIM, G
DANISHEFSKY, SJ
[J]. TETRAHEDRON LETTERS, 1989, 30 (28) : 3625 - 3628

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