Stereospecific syntheses of 5-alkyl-3-ethoxy-2-((phenylchalcogeno)methylene)tetrahydrofurans

被引：14

作者：

Yoshimatsu, M

Naito, M

Shimizu, H

Muraoka, O

Tanabe, G

Kataoka, T

机构：

[1] GIFU PHARMACEUT UNIV,GIFU 502,JAPAN

[2] KINKI UNIV,FAC PHARMACEUT SCI,HIGASHIOSAKA,OSAKA 577,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 23期

关键词：

D O I：

10.1021/jo961071c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Ethoxy-4-(phenylchalcogeno)but-3-ynyl ketones 1-10 were reduced with LiBH4 in Et(2)O diastereoselectively to give 5-(phenylchalcogeno)pent-4-yn-1-ols 11-20. Treatment of the phenylchalcogen-substituted alkynyl alcohols 11-20 with t-BuOK in t-BuOH provided useful (Z)-2-((phenylchalcogeno)methylene)tetrahydrofurans 21-31 stereoselectively.

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页码：8200 / 8206

页数：7

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共 33 条

[11]

Harding K. E., 1991, COMPREHENSIVE ORGANI, V4, P363

[12] PREPARATION OF BRIDGEHEAD SUBSTITUTED BICYCLO[3.3.0]OCTANE DERIVATIVES BY THE BF3-CENTER-DOT-OET(2)-CATALYZED REARRANGEMENT OF BICYCLO[3.2.1]OCT-6-EN-8-OLS [J].

HAYASHI, Y ;

USHIO, H ;

NARASAKA, K .

CHEMISTRY LETTERS, 1994, (02) :289-292

[13] NICKEL AND PALLADIUM-CATALYZED COUPLING OF VINYL SELENIDES WITH TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE - A NEW SYNTHESIS OF ALLYL SILANES [J].

HEVESI, L ;

HERMANS, B ;

ALLARD, C .

TETRAHEDRON LETTERS, 1994, 35 (36) :6729-6730

[14] PREPARATION AND REGIOSELECTIVE AND DIASTEREOSELECTIVE REACTIONS OF ALLYLIC ZIRCONIUM REAGENTS FROM ALLYLIC ETHER DERIVATIVES [J].

ITO, H ;

TAGUCHI, T ;

HANZAWA, Y .

TETRAHEDRON LETTERS, 1992, 33 (10) :1295-1298

[15] SYNTHESIS AND COORDINATION ABILITY OF SELENOALKYNES R-SE-CC-R' [J].

LANG, H ;

KELLER, H ;

IMHOF, W ;

MARTIN, S .

CHEMISCHE BERICHTE, 1990, 123 (03) :417-422

[16] INTRAMOLECULAR OXYPALLADATION AND CROSS-COUPLING OF ACETYLENIC ALKOXIDES [J].

LUO, FT ;

SCHREUDER, I ;

WANG, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2213-2215

[17] A HIGHLY SELECTIVE SYNTHESIS OF VERSATILE (E)-1-PHENYLTHIO VINYLSTANNANES [J].

MAGRIOTIS, PA ;

BROWN, JT ;

SCOTT, ME .

TETRAHEDRON LETTERS, 1991, 32 (38) :5047-5050

[18] ISOLATION AND CRYSTAL-STRUCTURE ANALYSIS OF A TITANIUM-TETRACHLORIDE 1,3-DIKETONE COMPLEX [J].

MAIER, G ;

SEIPP, U ;

BOESE, R .

TETRAHEDRON LETTERS, 1987, 28 (39) :4515-4516

[19] SKIPPED DIYNES .5. SECONDARY DIETHYNYLCARBINOLS, A BASE-CATALYZED YNNOL TO ENOL REARRANGEMENT, AND ULTRAVIOLET-SPECTRA AND CONJUGATION [J].

MIGLIORESE, KG ;

TANAKA, Y ;

MILLER, SI .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (06) :739-747

[20] STEREOCHEMICAL COURSE OF DIRECT RING CLOSURES OF COMPLEX HOMOALLYLIC ALCOHOLS TO SUBSTITUTED TETRAHYDROFURANS [J].

MIHELICH, ED ;

HITE, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7318-7319

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