THE REACTION OF BETA-(TRIMETHYLSILYL)ALKYL PHENYL SULFONES WITH OXIRANES - A METHOD FOR STEREOCONTROLLED SYNTHESIS OF HOMOALLYLIC ALCOHOLS

被引:16
作者
KABAT, MM [1 ]
WICHA, J [1 ]
机构
[1] POLISH ACAD SCI,INST ORGAN CHEM,UL KASPRZAKA 44,PL-01224 WARSAW,POLAND
关键词
D O I
10.1016/S0040-4039(00)74491-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of beta-trimethylsilylalkyl sulfones (4a-4b) with oxirane derivatives (5a - 5d, 9) followed by treatment of the immediate adducts with sodium hydride, affords O-trimethylsilyl homoallylic alcohols (7a - 7e, 11), mainly (Z) isomers.
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页码:1073 / 1076
页数:4
相关论文
共 21 条
[1]   A NEW ANION REARRANGEMENT INVOLVING SILYL MIGRATION TO OXYGEN [J].
BROOK, AG ;
CHRUSCIEL, JJ .
ORGANOMETALLICS, 1984, 3 (08) :1317-1318
[2]   STEREOSELECTIVE HOMOALLYLIC ALCOHOL SYNTHESIS VIA SULFONE ALPHA-CARBANION-MEDIATED COUPLING REACTIONS [J].
CRAIG, D ;
SMITH, AM .
TETRAHEDRON LETTERS, 1990, 31 (18) :2631-2632
[3]   REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES [J].
FINAN, JM ;
KISHI, Y .
TETRAHEDRON LETTERS, 1982, 23 (27) :2719-2722
[4]   THE REACTIONS OF TRIS(TRIMETHYLSILYL)METHYL-LITHIUM WITH SOME CARBON ELECTROPHILES [J].
FLEMING, I ;
FLOYD, CD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03) :969-976
[5]   1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHANE - A VALUABLE INTERMEDIATE FOR SYNTHESIS OF OLEFINS, ALLYLTRIMETHYLSILANES, BETA-TRIMETHYLSILYL KETONES, VINYL SULFONES, 2-(PHENYLSULFONYL)ALLYL ALCOHOLS, AND VARIED TRIMETHYLSILYL DERIVATIVES [J].
HSIAO, CN ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2688-2699
[6]  
HSIAO CN, 1982, TETRAHEDRON LETT, V24, P1963
[7]   STEREOSPECIFIC OLEFIN-FORMING ELIMINATION-REACTIONS OF BETA-HYDROXYALKYLSILANES [J].
HUDRLIK, PF ;
PETERSON, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1464-1468
[8]  
JANKOWSKI P, IN PRESS ORGANOMET C
[9]  
KOCIENSKI PJ, 1979, TETRAHEDRON LETT, V27, P2649
[10]   A PRACTICAL SYNTHESIS OF SEVERAL POLYHYDROXYLATED CHIRAL BUILDING-BLOCKS [J].
KUSAKABE, M ;
KATO, H ;
SATO, F .
CHEMISTRY LETTERS, 1987, (11) :2163-2166