DIISOPROPYL TARTRATE-MODIFIED (E)-GAMMA-[(MENTHOFURYL)DIMETHYLSILYL]ALLYLBORONATE, AN IMPROVED CHIRAL REAGENT FOR THE ANTI-ALPHA-HYDROXYALLYLATION OF ALDEHYDES - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (-)-SWAINSONINE

被引：30

作者：

HUNT, JA ^{[1
]}

ROUSH, WR ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 04期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(94)02295-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of anti 1,2-diols via the reactions of aldehydes and the tartrate ester-modified (E)-gamma-(menthofurylsilyl)allylboronate 5 has been developed. This methodology is applied to a brief, enantioselective synthesis of (-)-swainsonine.

引用

页码：501 / 504

页数：4

共 36 条

[1] METHODOLOGY TO ESTABLISH 1,2-DIFUNCTIONALITY AND 1,3-DIFUNCTIONALITY FOR THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES
AGER, DJ
EAST, MB
[J]. TETRAHEDRON, 1992, 48 (14) : 2803 - 2894
[2] B-[3-((DIISOPROPYLAMINO)DIMETHYLSILYL)ALLYL]DIISOPINOCAMPHEYLBORANE - AN EXCELLENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI VICINAL DIOLS
BARRETT, AGM
MALECHA, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) : 5243 - 5245
[3] A SHORT, ENANTIOSELECTIVE SYNTHESIS OF (-)-SWAINSONINE
BENNETT, RB
CHOI, JR
MONTGOMERY, WD
CHA, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2580 - 2582
[4] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT
BORCH, RF
BERNSTEIN, MD
DURST, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) : 2897 - +
[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .13. A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ADDITION OF [(Z)-GAMMA-ALKOXYALLYL]DIISOPINOCAMPHEYLBORANES TO ALDEHYDES
BROWN, HC
JADHAV, PK
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1535 - 1538
[6] BROWN HC, 1994, UNPUB J ORG CHEM
[7] DIBELLO IC, 1989, BIOCHEM J, V259, P855
[8] EARBORN C, 1961, J CHEM SOC, P4921
[9] GLYCOSIDASE INHIBITORS - INHIBITORS OF N-LINKED OLIGOSACCHARIDE PROCESSING
ELBEIN, AD
[J]. FASEB JOURNAL, 1991, 5 (15) : 3055 - 3063
[10] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED FORM OF THE HYDROXY GROUP
FLEMING, I
HENNING, R
PLAUT, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) : 29 - 31

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