A NOVEL ENTRY INTO WITTIG REARRANGEMENTS - A STEREOSELECTIVE [1,2]-WITTIG REARRANGEMENT WITH INVERSION OF CONFIGURATION AT THE CARBANION CENTER

被引：28

作者：

HOFFMANN, R ^{[1
]}

BRUCKNER, R ^{[1
]}

机构：

[1] UNIV WURZBURG, INST ORGAN CHEM, AM HUBLAND, W-8700 WURZBURG, GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 08期

关键词：

CARBANIONS; CONFIGURATIONAL STABILITY; DIASTEREOSELECTIVITY; 1,2]-WITTIG REARRANGEMENT;

D O I：

10.1002/cber.19921250824

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The O,Se-ketal 10, through lithium naphthalenide induced reductive cleavage of its C(sp3) - Se bond, was converted into the alpha-lithio ether 11a with an equatorially oriented C - O bond. At -78-degrees-C, 11 a undergoes a rapid [1,2]-Wittig rearrangement to provide stereoselectively the homoallylic alcohol 12a with an axial OH group. Thus, the rearrangement proceeds with inversion of configuration at the carbanion center.

引用

页码：1957 / 1963

页数：7

共 44 条

[1] [Anonymous], 1970, ANGEW CHEM, V82, P795
[2] WITTIG REARRANGEMENT OF AROMATIC ACETALS AND KETALS INDUCED BY REDUCTIVE ELECTRON-TRANSFER
AZZENA, U
DENURRA, T
MELLONI, G
PIRODDI, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) : 5532 - 5535
[3] BALDWIN JE, 1970, TETRAHEDRON LETT, P353
[4] SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT
BOL, KM
LISKAMP, RMJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (39) : 5401 - 5404
[5] BRIERE R, 1977, TETRAHEDRON LETT, P3489
[6] REDUCTIVE LITHIATION MEDIATED ANIONIC CYCLIZATIONS AND [2,3]-SIGMATROPIC REARRANGEMENTS
BROKA, CA
SHEN, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) : 2981 - 2984
[7] SYNTHESIS OF (ALKOXYMETHYL)ZIRCONOCENE CHLORIDES - STEREOCHEMISTRY OF CARBON CARBON BOND FORMATION IN A ZIRCONOCENE-WITTIG REARRANGEMENT
BUCHWALD, SL
NIELSEN, RB
DEWAN, JC
[J]. ORGANOMETALLICS, 1989, 8 (07) : 1593 - 1598
[8] ORGANOALKALI COMPOUNDS BY RADICAL-ANION INDUCED REDUCTIVE METALATION OF PHENYL THIOETHERS
COHEN, T
BHUPATHY, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) : 152 - 161
[9] 2-FLASK PREPARATION OF ALPHA-LITHIO CYCLIC ETHERS FROM GAMMA-LACTONES AND DELTA-LACTONES - REDUCTIVE LITHIATION AS A ROUTE, VIA RADICAL INTERMEDIATES, TO AXIAL 2-LITHIOTETRAHYDROPYRANS AND THEIR EQUILIBRATION TO THE EQUATORIAL ISOMERS
COHEN, T
LIN, MT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) : 1130 - 1131
[10] DYNAMIC SE-77 NMR OF PHENYLSELENYL CYCLOHEXANE DERIVATIVES
DUDDECK, H
WAGNER, P
GEGNER, S
[J]. TETRAHEDRON LETTERS, 1985, 26 (09) : 1205 - 1208

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