THE FIRST EXAMPLE OF CHIRALITY TRANSFER IN ALLYLIC TELLUROXIDES - POSSIBLE [2,3]-SIGMATROPIC REARRANGEMENT

被引：29

作者：

CHIBA, T ^{[1
]}

NISHIBAYASHI, Y ^{[1
]}

SINGH, JD ^{[1
]}

OHE, K ^{[1
]}

UEMURA, S ^{[1
]}

机构：

[1] KYOTO UNIV,GRAD SCH ENGN,DIV ENERGY & HYDROCARBON CHEM,SAKYO KU,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 09期

关键词：

D O I：

10.1016/0040-4039(95)00074-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

t-Butyl hydroperoxide or aerial oxidation of four allylic chiral ferrocenyl tellurides derived from (S,R)- and (R,S)-di[2-(1-dimethylaminoethyl)ferrocenyl] ditellurides produces the corresponding chiral allylic alcohols in 14-22% enantiomeric excess by chirality transfer via possible [2,3]-sigmatropic rearrangement of the intermediate allylic telluroxides.

引用

页码：1519 / 1522

页数：4

共 15 条

[1] ASYMMETRIC OXIDATION OF SIMPLE SELENIDES TO SELENOXIDES IN HIGH ENANTIOPURITY - STEREOCHEMICAL ASPECTS OF THE ALLYL SELENOXIDE ALLYL SELENENATE REARRANGEMENT [J].

DAVIS, FA ;

REDDY, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2599-2606

[2] OXIDATION OF SELENIDES AND TELLURIDES WITH POSITIVE HALOGENATING SPECIES [J].

DETTY, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02) :274-279

[3] ORGANOTELLURIUMS .14. TRANSFORMATION OF ALLYLSILANES INTO ALLYLAMINES VIA PHENYLTELLURINYLATION [J].

HU, NX ;

ASO, Y ;

OTSUBO, T ;

OGURA, F .

TETRAHEDRON LETTERS, 1988, 29 (39) :4949-4952

[4] THE 1ST EXAMPLE OF ASYMMETRIC SELENOXIDE ELIMINATION - APPLICATION TO THE SYNTHESIS OF CHIRAL ALLENES [J].

KOMATSU, N ;

NISHIBAYASHI, Y ;

SUGITA, T ;

UEMURA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (01) :46-47

[5] ASYMMETRIC SELENOXIDE ELIMINATION LEADING TO CHIRAL ALKYL AND ARYL CYCLOHEXYLIDENEMETHYL KETONES [J].

KOMATSU, N ;

MATSUNAGA, S ;

SUGITA, T ;

UEMURA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5847-5848

[6] ASYMMETRIC SELENOXIDE ELIMINATION LEADING TO CHIRAL ALLENIC SULFONES [J].

KOMATSU, N ;

MURAKAMI, T ;

NISHIBAYASHI, Y ;

SUGITA, T ;

UEMURA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3697-3702

[7] ASYMMETRIC [2,3] SIGMATROPIC REARRANGEMENT VIA CHIRAL SELENOXIDE WITH SHARPLESS OXIDANTS [J].

KOMATSU, N ;

NISHIBAYASHI, Y ;

UEMURA, S .

TETRAHEDRON LETTERS, 1993, 34 (14) :2339-2342

[8] SYNTHESIS OF CHIRAL DIFERROCENYL DISELENIDES AND THEIR APPLICATION TO ASYMMETRIC REACTIONS [J].

NISHIBAYASHI, Y ;

SINGH, JD ;

UEMURA, S ;

FUKUZAWA, S .

TETRAHEDRON LETTERS, 1994, 35 (19) :3115-3118

[9] SYNTHESES AND REACTIVITIES OF FERROCENYL ORGANYL TELLURIDES [J].

NISHIBAYASHI, Y ;

CHIBA, T ;

SINGH, JD ;

UEMURA, S ;

FUKUZAWA, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 473 (1-2) :205-213

[10]

NISHIBAYASHI Y, 1993, 40TH S ORG CHEM SAPP, pB202

← 1 2 →