INTRAMOLECULAR AMIDOALKYLATION OF CHIRAL IMINIUM IONS - STEREOSELECTIVE SYNTHESIS OF SYN-1,3-AMINOALCOHOLS

被引：24

作者：

HIOKI, H

OKUDA, M

MIYAGI, W

ITO, S

机构：

[1] Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, 770, Yamashirocho

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)61748-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Hosomi-Sakurai reaction of 3-siloxybutaniminium salts exhibited a syn selectivity of up to 51:1, while the same type of reaction of 2-methyl-3-siloxypropaniminium salts showed up to 290:1 syn selectivity.

引用

页码：6131 / 6134

页数：4

共 7 条

[1] SILICON DIRECTED N-ACYLIMINIUM ION CYCLIZATIONS - HIGHLY SELECTIVE SYNTHESES OF (+/-)-ISORETRONECANOL AND (+/-)-EPILUPININE [J].

HIEMSTRA, H ;

SNO, MHAM ;

VIJN, RJ ;

SPECKAMP, WN .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4014-4020

[2] INTRAMOLECULAR REACTIONS OF ACYCLIC N-ACYLIMINIUM IONS .2. ALLYL SILANES AS NUCLEOPHILES [J].

HIEMSTRA, H ;

FORTGENS, HP ;

SPECKAMP, WN .

TETRAHEDRON LETTERS, 1985, 26 (26) :3155-3158

[3] CARBAMATE-MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .3. INTRAMOLECULAR MICHAEL ADDITION OF O-CARBAMATES TO ALPHA,BETA-UNSATURATED ESTERS - A NEW DIASTEREOSELECTIVE AMINATION IN AN ACYCLIC SYSTEM [J].

HIRAMA, M ;

SHIGEMOTO, T ;

YAMAZAKI, Y ;

ITO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1797-1798

[4] ACYCLIC STEREOSELECTION .20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY ALDEHYDES [J].

KIYOOKA, S ;

HEATHCOCK, CH .

TETRAHEDRON LETTERS, 1983, 24 (44) :4765-4768

[5] TOTAL SYNTHESIS OF (+/-)-ALPHA-ALLOKAINIC ACID VIA 2 ALLYLSILANE N-ACYLIMINIUM ION REACTIONS [J].

MOOIWEER, HH ;

HIEMSTRA, H ;

SPECKAMP, WN .

TETRAHEDRON, 1991, 47 (20-21) :3451-3462

[6] STEREOSELECTIVE INTRAMOLECULAR ALLYLSILANE ADDITIONS TO CHIRAL ALDEHYDES [J].

REETZ, MT ;

JUNG, A ;

BOLM, C .

TETRAHEDRON, 1988, 44 (13) :3889-3898

[7] SELECTIVE REACTIONS OF ORGANOTITANIUM REAGENTS [J].

REETZ, MT .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1781-1788

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