A CONVENIENT SYNTHESIS OF 3,4-BIS(TRIMETHYLSILYLMETHYL)-5,6-DIHYDRO-2H-PYRANS THROUGH A CATALYZED HETERO-DIELS-ALDER REACTION

被引：7

作者：

BROUARD, C ^{[1
]}

PORNET, J ^{[1
]}

MIGINIAC, L ^{[1
]}

机构：

[1] UNIV POITIERS,SYNTHESE ORGAN LAB,CNRS,URA 574,40 AVE RECTEUR PINEAU,F-86022 POITIERS,FRANCE

来源：

SYNTHETIC COMMUNICATIONS | 1994年 / 24卷 / 21期

关键词：

D O I：

10.1080/00397919408011317

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of boron trifluoride etherate, 2,3-bis(trimethylsilylmethyl)-1,3-butadiene reacts with aldehydes and ketones to lead generally to an only product, resulting from an hetero Diels-Alder reaction.

引用

页码：3047 / 3053

页数：7

共 13 条

[1]

BRANDSMA L, 1988, PREPARATIVE ACETYLEN, P256

[2] MARINE NATURAL-PRODUCTS - METABOLITES OF MARINE-ALGAE AND HERBIVOROUS MARINE MOLLUSKS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1984, 1 (03) :251-280

[3]

Fleming I., 1989, ORG REACTIONS, V37, P57

[4] LITHIUM CATALYZED HETERO-DIELS-ALDER REACTIONS CYCLOCONDENSATION OF N-PROTECTED ALPHA-AMINO ALDEHYDES WITH 1-METHOXY-3-TERT-BUTYLDIMETHYLSILYLOXYBUTADIENE IN THE PRESENCE OF LITHIUM PERCHLORATE [J].

GRIECO, PA ;

MOHER, ED .

TETRAHEDRON LETTERS, 1993, 34 (35) :5567-5570

[5] 2-TRIMETHYLSILYLMETHYL ALLYLTRIMETHYLSILANE, PRECURSOR OF CARBOCYCLES AND HETEROCYCLES WITH A METHYLENE GROUP [J].

GUYOT, B ;

PORNET, J ;

MIGINIAC, L .

TETRAHEDRON, 1991, 47 (24) :3981-3988

[6]

KLEIJN H, 1980, RECL TRAV CHIM PAY B, V99, P340

[7] [(TRIMETHYLSILYL)METHYL]COPPER(I) SPECIES - VERSATILE REAGENTS TO PREPARE FUNCTIONALLY SUBSTITUTED ALLYLIC SILANES [J].

KLEIJN, H ;

VERMEER, P .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5143-5148

[8] ALLYLSILANE INITIATED CARBOCYCLIZATIONS [J].

MAJETICH, G ;

DESMOND, R ;

CASARES, AM .

TETRAHEDRON LETTERS, 1983, 24 (18) :1913-1916

[9] ALLYLSILANE-INITIATED CYCLOPENTANE ANNULATIONS [J].

MAJETICH, G ;

DESMOND, RW ;

SORIA, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1753-1769

[10]

SAVER J, 1966, ANGEW CHEM INT EDIT, V5, P211

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