HIGHLY STEREOSELECTIVE CHELATION CONTROLLED ENE-REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHERS

被引：26

作者：

NAKAMURA, T ^{[1
]}

TANINO, K ^{[1
]}

KUWAJIMA, I ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM,TOKYO 152,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 03期

关键词：

D O I：

10.1016/0040-4039(93)85106-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under the chelation conditions the title compounds reacted with alpha-benzyloxyaldehyde to afford syn diol exclusively. Further, three contiguous diastercomeric centers were constructed with high stereoselectivity by using (E) or (Z)-crotyl silyl ether. This methodology was applied to the stereoselective synthesis of brassinolide side chain.

引用

页码：477 / 480

页数：4

共 36 条

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CHEMISTRY LETTERS, 1986, (11) : 1817 - 1820
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Shiina, I
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TETRAHEDRON LETTERS, 2002, 43 (36) : 6391 - 6394
[16] ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS
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[17] Synthesis of 2-(arylsulfonyl)-4-hydroxypyridines by hetero-Diels-Alder reaction of 1,3-bis-silyl enol ethers with arylsulfonyl cyanides
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SYNTHESIS-STUTTGART, 2006, (15): : 2551 - 2555
[18] [1,1'-BI-2-NAPHTHALENEDIOLATO(2-)-O,O']OXOTITANIUM - AN EFFICIENT CHIRAL-CATALYST FOR THE ASYMMETRIC ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES
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[19] CHELATION-CONTROLLED NUCLEOPHILIC ADDITIONS .2. HIGHLY EFFECTIVE SYSTEM FOR ASYMMETRIC INDUCTION IN THE REACTION OF ORGANOMETALLICS WITH BETA-ALKOXYALDEHYDES
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TETRAHEDRON LETTERS, 1980, 21 (11) : 1035 - 1038
[20] InBr3-Catalyzed Coupling Reaction between Electron-Deficient Alkenyl Ethers with Silyl Enolates for Stereoselective Synthesis of 1,5-Dioxo-alk-2-enes
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