SILICON-DIRECTED DIENE SYNTHESIS

被引：27

作者：

BROWN, PA ^{[1
]}

BONNERT, RV ^{[1
]}

JENKINS, PR ^{[1
]}

LAWRENCE, NJ ^{[1
]}

SELIM, MR ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期

关键词：

D O I：

10.1039/p19910001893

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of 2-substituted-1,3-dienes is reported which uses silicon as a control element: Eight aldehydes were converted into alpha-silyl ketones by treatment with trimethylsilylmethylmagnesium chloride and rapid Collins oxidation. Addition of vinylmagnesium bromide to the resulting alpha-silyl ketones, followed by Peterson elimination, gave a series of dienes. The route was used to make (4S)-3-methylene-t-[(phenylmethoxy)methoxy]pent-1-ene from (-)-ethyl lactate; low asymmetric induction was observed in the Diels-Alder reactions of this diene with diethyl fumarate and N-phenylmaleimide.

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页码：1893 / 1900

页数：8

相关论文

共 64 条

[11] FORMATION OF VINYLSILANES AND ALLYLSILANES IN THERMAL ELIMINATION-REACTIONS OF ESTERS OF BETA-HYDROXYALKYLTRIMETHYLSILANES [J].

CAREY, FA ;

TOLER, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (11) :1966-1971

[12] ALLYL SILANES IN ORGANIC-SYNTHESIS - SOME REACTIONS OF 3-TRIMETHYLSILYLCYCLOHEX-4-ENE-1,2-DICARBOXYLIC ACID AND ITS DERIVATIVES [J].

CARTER, MJ ;

FLEMING, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (17) :679-680

[13] THE SYNTHESIS OF ALKENES FROM CARBONYL-COMPOUNDS AND CARBANIONS-ALPHA TO SILICON - STEREOSELECTIVE SYNTHESIS OF 1-TRIMETHYLSILYLBUTA-1,3-DIENES [J].

CHAN, TH ;

LI, JS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (17) :969-970

[14]

CHAN TH, 1970, TETRAHEDRON LETT, P1137

[15]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[16] A GENERAL PROCEDURE FOR PREPARING ALPHA-LITHIOSILANES - GENERALIZATION OF THE PETERSON OLEFINATION [J].

COHEN, T ;

SHERBINE, JP ;

MATZ, JR ;

HUTCHINS, RR ;

MCHENRY, BM ;

WILLEY, PR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) :3245-3252

[17] DIELS-ALDER REACTIONS OF 4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE [J].

COOKSON, RC ;

GILANI, SSH ;

STEVENS, IDR .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (19) :1905-+

[18] ALLYLIC SILICON-CONTAINING ORGANOMETALLIC COMPOUNDS OBTAINMENT AND BEHAVIOR [J].

CORRIU, R ;

MASSE, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 57 (01) :C5-C8

[19] STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].

CRAM, DJ ;

ELHAFEZ, FAA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5828-5835

[20] ORGANIC-REACTIONS AT HIGH-PRESSURE - ASYMMETRIC INDUCTION IN THE DIELS-ALDER REACTION OF PARA-BENZOQUINONE WITH CHIRAL 2,4-PENTADIENOIC ACID-DERIVATIVES [J].

DAUBEN, WG ;

BUNCE, RA .

TETRAHEDRON LETTERS, 1982, 23 (47) :4875-4878

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