HIGHLY STEREOSELECTIVE PREPARATION OF NITRO-OLEFINS AND NITRO-DIENES BY THE ADDITION-ELIMINATION OF COPPER-ZINC ORGANOMETALLICS TO BETA-ALKYLTHIO AND BETA-PHENYLSULFONYL NITRO OLEFINS

被引：32

作者：

RETHERFORD, C ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MICHIGAN,DEPT CHEM,WILLARD H DOW LABS,ANN ARBOR,MI 48109

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(00)79462-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition-elimination of copper-zinc organometallics RCu(CN)ZnX to (E)-1-nitro-2-phenysulfonyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. beta-Alkylthio nitro olefins such as 2-ethylthio-1-nitro-1-cyclohexene 2b and 2,2-dimethylthio-1-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica gel-catalyzed, stereospecific Diels-Alder cyclization.

引用

页码：441 / 444

页数：4

共 43 条

[1] Alexakis A, 1984, ORG SYNTH, V62, P1
[2] 1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC-SYNTHESIS - THE PREPARATION OF ALKYL-SUBSTITUTED AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION-GRIGNARD REACTION-DESULFONYLATION SEQUENCE
AZZENA, U
COSSU, S
DELUCCHI, O
MELLONI, G
[J]. TETRAHEDRON LETTERS, 1989, 30 (14) : 1845 - 1848
[3] SELENOSULFONATION OF ACETYLENES - SUBSTITUTION-REACTIONS OF BETA-(PHENYLSELENO)VINYL SULFONES WITH ORGANOCUPRATES
BACK, TG
COLLINS, S
LAW, KW
[J]. TETRAHEDRON LETTERS, 1984, 25 (16) : 1689 - 1692
[4] GENERAL-APPROACH TO HIGHLY FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER
BERK, SC
KNOCHEL, P
YEH, MCP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) : 5789 - 5791
[5] BLOOM AJ, 1986, TETRAHEDRON LETT, V27, P873
[6] CAHIEZ G, 1976, SYNTHESIS-STUTTGART, P245
[7] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[8] DIAZOTATIVE DEAMINOSILYLATION OF BETA-AMINO SILANES
CUNICO, RF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) : 4474 - 4478
[9] SYNTHETIC EXPLOITATION OF THE RING-OPENING OF 3,4-DINITROTHIOPHENE - A NOVEL ACCESS TO 1,4-DIALKYL-2,3-DINITRO-1,3-BUTADIENES AND 1,4-DIARYL-2,3-DINITRO-1,3-BUTADIENES
DELLERBA, C
MELE, A
NOVI, M
PETRILLO, G
STAGNARO, P
[J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4933 - 4936
[10] STEREOSELECTIVITY IN THE ADDITION OF ORGANOCUPRATES TO BETA-ALKYLTHIO ALPHA,BETA-ENONES
DIETER, RK
SILKS, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (16) : 2786 - 2788

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