REDUCTIVE DESULFURIZATION OF SULTONES PREPARED VIA INTRAMOLECULAR DIELS-ALDER REACTION OF A FURAN-CONTAINING VINYLSULFONATE

被引：31

作者：

METZ, P

CRAMER, E

机构：

[1] Organisch-Chemisches Institut der Universität Münster, D-48149 Münster

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 40期

关键词：

D O I：

10.1016/0040-4039(93)85048-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of sultone 1 and the saturated derivative 3 with strong bases or reaction of 1 with Red-Al caused a cleavage of the oxygen bridge. The resultant vinylic or allylic sultones 4 and 5 were efficiently desulfurized by metal/ammonia reduction. While a mixture of cyclohexenes 6 and 7 was produced from allylic sultones 5, the vinylic sultones 4 reacted with complete regioselectivity to yield only 7.

引用

页码：6371 / 6374

页数：4

共 19 条

[1] STRAIN-DIRECTED BRIDGE CLEAVAGE OF (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - APPLICATION TO THE TOTAL SYNTHESIS OF CARBA-ALPHA-DL-GLUCOPYRANOSE
ACENA, JL
ARJONA, O
DELAPRADILLA, RF
PLUMET, J
VISO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 1945 - 1946
[2] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF HYDROXYCYCLOHEXENYL SULFONES FROM OXANORBORNENES
ARJONA, O
DELAPRADILLA, RF
MALLO, A
PLUMET, J
VISO, A
[J]. TETRAHEDRON LETTERS, 1990, 31 (10) : 1475 - 1478
[3] INTRAMOLECULAR DIELS-ALDER REACTION OF VINYLSULFONIC ACID-ESTERS
BOVENSCHULTE, E
METZ, P
HENKEL, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02): : 202 - 203
[4] BOVENSCHULTE E, 1989, ANGEW CHEM, V101, P204
[5] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL TRIENES - DIENOPHILE-CONTROLLED CYCLOADDITIONS OF MATCHED AND UNMATCHED DIMETHYLATED SUBSTRATES
CRAIG, D
READER, JC
[J]. TETRAHEDRON LETTERS, 1992, 33 (41) : 6165 - 6168
[6] REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES
FINAN, JM
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1982, 23 (27) : 2719 - 2722
[7] GUILFORD AJ, 1983, J CHEM SOC CHEM COMM, P46
[8] EFFECTS OF NEIGHBORING HYDROXY-GROUPS IN METAL-AMMONIA REDUCTIONS OF ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS
IWATA, C
MIYASHITA, K
IDA, Y
YAMADA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (10) : 461 - 463
[9] RING-OPENING REACTIONS OF OXABICYCLIC COMPOUNDS AS A ROUTE TO CYCLIC AND ACYCLIC COMPOUNDS WITH MULTIPLE STEREOCENTERS
LAUTENS, M
[J]. SYNLETT, 1993, (03) : 177 - 185
[10] SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .2. SIMPLE DEOXYALDITOLS
MA, P
MARTIN, VS
MASAMUNE, S
SHARPLESS, KB
VITI, SM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) : 1378 - 1380

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