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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[25] CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF ENOL ETHERS WITH ARYL TRIFLATES - LIGAND CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION OF [2-(DIMETHYLAMINO)ETHOXY]ETHENE
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ANDERSSON, CM
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[26] Highly stereoselective trifluoropyruvate-ene reaction with Δ20(22)-steroidal olefin by chiral Pd2+-catalyst: New type of VDR antagonist for osteocalcin, Δ20(21)-ene product without (dehydro)lactone and lactam motifs
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[27] CHELATION-CONTROLLED AND NON-CHELATION-CONTROLLED ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO ALPHA-AMINO ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF THE BETA-AMINO-ALPHA-HYDROXY ALDEHYDE INTERMEDIATE FOR THE PREPARATION OF THE HUMAN-IMMUNODEFICIENCY-VIRUS PROTEINASE-INHIBITOR RO-31-8959
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