EFFICIENT, TRIMETHYLSILYL TRIFLATE MEDIATED CONVERSION OF DIELS-ALDER ADDUCTS OF 1-METHOXY-3[(TRIMETHYLSILYL)OXY]-1,3-BUTADIENE (DANISHEFSKYS DIENE) TO CYCLOHEXENONES

被引：26

作者：

VORNDAM, PE ^{[1
]}

机构：

[1] UNIV COLORADO,DEPT CHEM & BIOCHEM,BOULDER,CO 80309

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 11期

关键词：

D O I：

10.1021/jo00298a066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Since its introduction in 1974,2l-methoxy-3-[(trimethylsilyl)oxy]-l,3-butadiene (Danishefsky’s diene, 1) has been successfully employed in a wide variety of synthetic efforts.3-6The foremost synthetic application of 1 continues to be the Diels-Alder synthesis of cyclohexenones. © 1990, American Chemical Society. All rights reserved.

引用

页码：3693 / 3695

页数：3

共 24 条

[1] DIELS-ALDER REACTION OF SOME TRIMETHYLSILYLOXY 1,3-DIENES [J].

BELANGER, J ;

LANDRY, NL ;

PARE, JRJ ;

JANKOWSKI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3649-3652

[2] SILOXY DIENES IN TOTAL SYNTHESIS [J].

DANISHEFSKY, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :400-406

[3]

EMDE H, 1982, SYNTHESIS-STUTTGART, P1

[4]

HARVEY DF, 1984, J AM CHEM SOC, V106, P2455

[5]

HIRAMA M, 1979, J AM CHEM SOC, V101, P7020

[6]

HOLMES AM, 1982, CAN J CHEM, V60, P308

[7] REGIOCONTROLLED SYNTHESIS OF MONOSUBSTITUTED, DISUBSTITUTED, AND TRISUBSTITUTED CYCLOHEXENONES BY CYCLOADDITION OF VINYL SULFONES TO 1-METHOXY-3-[(TRIMETHYLSILYL)OXY]-1,3-BUTADIENES - CONVERSION OF ALKENES INTO EFFECTIVE DIENOPHILIC REAGENTS [J].

KINNEY, WA ;

CROUSE, GD ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4986-5000

[8]

KITAHARA T, 1983, ORG SYNTH, V61, P147

[9]

KITAHARA T, 1974, J AM CHEM SOC, V96, P7807

[10]

KITAHARA T, 1979, J AM CHEM SOC, V101, P6996

← 1 2 3 →