Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans.

被引：34

作者：

Andrey, O ^{[1
]}

Ducry, L ^{[1
]}

Landais, Y ^{[1
]}

Planchenault, D ^{[1
]}

Weber, V ^{[1
]}

机构：

[1] UNIV LAUSANNE,COLL PROPEDEUT,INST CHIM ORGAN,CH-1015 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 12期

关键词：

ALDOL-CYCLIZATION SEQUENCE; ALPHA-SILYLACETIC ESTERS; SUBSTITUTED TETRAHYDROFURANS; HOMOALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSPECIFIC SYNTHESIS; SILAFUNCTIONAL COMPOUNDS; ORGANOTIN COMPOUNDS; SILICON;

D O I：

10.1016/S0040-4020(97)00109-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised was shown to be oxidized under both electrophilic and nucleophilic conditions. (C) 1997 Elsevier Science Ltd.

引用

页码：4339 / 4352

页数：14

共 53 条

[21] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED OXETANES [J].

GALATSIS, P ;

PARKS, DJ .

TETRAHEDRON LETTERS, 1994, 35 (36) :6611-6614

[22]

GALATSIS P, 1995, TETRAHEDRON LETT, V36, P8179, DOI 10.1016/00404-0399(50)1798M-

[23] REACTIVITY OF ALLYL ORGANOTIN COMPOUNDS WITH HALOGEN DERIVATIVES - SYNTHESIS AND MECHANISM [J].

GRIGNON, J ;

SERVENS, C ;

PEREYRE, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 96 (02) :225-235

[24] SUBSTITUTION MECHANISM OF DERIVATIVES HALOGENATED BY ALLYLIC ORGANOTIN COMPOUNDS [J].

GRIGNON, J ;

PEREYRE, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 61 (01) :C33-C35

[25] STEREOSELECTIVITY IN INTRAMOLECULAR AMIDOMERCURATION - KINETIC VS THERMODYNAMIC CONTROL [J].

HARDING, KE ;

MARMAN, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2838-2840

[26] STEREOSELECTIVE SYNTHESIS OF (+/-)-ERYTHRO- AND THREO-GAMMA-HYDROXYNORVALINE [J].

HARDING, KE ;

MARMAN, TH ;

NAM, DH .

TETRAHEDRON LETTERS, 1988, 29 (14) :1627-1630

[27] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS [J].

HOFFMANN, RW .

CHEMICAL REVIEWS, 1989, 89 (08) :1841-1860

[28]

JONES AD, 1996, J CHEM SOC CHEM COMM, P915

[29] The oxidation of the carbon-silicon bond [J].

Jones, GR ;

Landais, Y .

TETRAHEDRON, 1996, 52 (22) :7599-7662

[30] MODELING CHEMICAL-REACTIVITY .4. REGIOCHEMISTRY AND STEREOCHEMISTRY OF ELECTROPHILIC ADDITIONS TO ALLYLIC DOUBLE-BONDS [J].

KAHN, SD ;

PAU, CF ;

CHAMBERLIN, AR ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :650-663

← 1 2 3 4 5 6 →