A sequence of palladium-catalyzed borylation of allyl acetates with bis(pinacolato)diboron and intramolecular allylboration for the cyclization of oxo-2-alkenyl acetates

被引：40

作者：

Ahiko, TA ^{[1
]}

Ishiyama, T ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] HOKKAIDO UNIV, GRAD SCH ENGN, DIV MOL CHEM, SAPPORO, HOKKAIDO 060, JAPAN

来源：

CHEMISTRY LETTERS | 1997年 / 08期

关键词：

D O I：

10.1246/cl.1997.811

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cross-coupling reaction of bis(pinacolato)diboron with oxo-2-alkenyl acetates in toluene at 50 degrees C in the presence of Pd(dba)(2)/2 AsPh3 (3 mol%) to give allylboronates was followed by the intramolecular allylboration at 100 degrees C. The sequence provided cyclic homoallyl alcohols in high yields.

引用

页码：811 / 812

页数：2

共 18 条

[1] STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES [J].

DENMARK, SE ;

WEBER, EJ ;

WILSON, TM ;

WILLSON, TM .

TETRAHEDRON, 1989, 45 (04) :1053-1065

[2] STEREOCHEMISTRY OF SOME REACTIONS BETWEEN ALLYLIC AND SATURATED GRIGNARD REAGENTS AND ALDEHYDES [J].

FELKIN, H ;

GAULT, Y ;

ROUSSI, G .

TETRAHEDRON, 1970, 26 (15) :3761-&

[3]

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

[4] CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION [J].

GEVORGYAN, V ;

KADOTA, I ;

YAMAMOTO, Y .

TETRAHEDRON LETTERS, 1993, 34 (08) :1313-1316

[5]

Hoffmann RW, 1996, LIEBIGS ANN, P1283

[6]

HOFFMANN RW, 1991, LIEBIGS ANN CHEM, P1195

[7] A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates [J].

Ishiyama, T ;

Ahiko, T ;

Miyaura, N .

TETRAHEDRON LETTERS, 1996, 37 (38) :6889-6892

[8] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates [J].

Ishiyama, T ;

Itoh, Y ;

Kitano, T ;

Miyaura, N .

TETRAHEDRON LETTERS, 1997, 38 (19) :3447-3450

[9] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].

ISHIYAMA, T ;

MURATA, M ;

MIYAURA, N .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510

[10]

KECK GE, 1995, J AM CHEM SOC, V117, P6120

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