Allyldimethyltritylsilane. Synthesis of cyclopentanols, oxetanes, and tetrahydrofurans by reaction with electron deficient olefins

被引：51

作者：

Groaning, MD ^{[1
]}

Brengel, GP ^{[1
]}

Meyers, AI ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 16期

关键词：

D O I：

10.1021/jo9805652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Same preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.

引用

页码：5517 / 5522

页数：6

共 23 条

[1]

AGER DJ, 1977, J CHEM RES MINIPRINT, P136

[2] ASYMMETRIC-SYNTHESIS OF TETRAHYDROFURANS BY DIASTEREOSELECTIVE [3+2]-CYCLOADDITION OF ALLYLSILANES WITH ALPHA-KETO ESTERS BEARING AN OPTICALLY-ACTIVE CYCLITOL AS A CHIRAL AUXILIARY [J].

AKIYAMA, T ;

YASUSA, T ;

ISHIKAWA, K ;

OZAKI, S .

TETRAHEDRON LETTERS, 1994, 35 (45) :8401-8404

[3]

Akiyama T, 1996, SYNLETT, P1095

[4] Tritylallyldimethylsilane-TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols [J].

Brengel, GP ;

Meyers, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3230-3231

[5] [2+2]-CYCLOADDITION AND [3+2]-CYCLOADDITION OF TRIISOPROPYLALLYLSILANE TO ALPHA,BETA-UNSATURATED BICYCLIC LACTAMS [J].

BRENGEL, GP ;

RITHNER, C ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5144-5146

[6] STEREOCHEMICAL COURSE OF THE ALLYSILANE BASED CYCLOPENTANE ANNULATION [J].

DANHEISER, RL ;

TAKAHASHI, T ;

BERTOK, B ;

DIXON, BR .

TETRAHEDRON LETTERS, 1993, 34 (24) :3845-3848

[7] Stereochemical control in organic synthesis using silicon-containing compounds [J].

Fleming, I ;

Barbero, A ;

Walter, D .

CHEMICAL REVIEWS, 1997, 97 (06) :2063-2192

[8]

FLEMING I, 1996, CHEMTRACTS ORG CHEM, V9, P1

[9] LATENT ACETONYLATION OF ALPHA,BETA-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE - SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES [J].

HOSOMI, A ;

KOBAYASHI, H ;

SAKURAI, H .

TETRAHEDRON LETTERS, 1980, 21 (10) :955-958

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

Jones, GR ;

Landais, Y .

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

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