Realization of high regioselectivity in the coupling reaction of a cyclopentadiene monoepoxide equivalent and aryl nucleophiles

被引：30

作者：

Kobayashi, Y ^{[1
]}

Takahisa, E ^{[1
]}

Usmani, SB ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 226, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10654-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Coupling reaction of monoacetate 2 and aryl hard nucleophiles is realized for the first time, which consists of the lithium arylborates as hard nucleophiles and NiCl2(PPh3)(2) as a catalyst. More importantly, the independent effects of t-BuCN and NaI and their synergistic function are discovered to increase regioselectivity furnishing trans 1,3-isomers 6 as the major products. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：597 / 600

页数：4

相关论文

共 27 条

[1]

Deardorff D. R., 1993, ORG SYNTH, VVIII, P13

[2] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486

[3] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].

FARINA, V ;

KRISHNAN, B ;

MARSHALL, DR ;

ROTH, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444

[4] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].

FARINA, V ;

KRISHNAN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595

[5] NICKEL-CATALYZED, CHLOROTRIALKYLSILANE-ASSISTED CONJUGATE ADDITION OF ALKENYLTRIBUTYLTIN REAGENTS TO ALPHA,BETA-UNSATURATED ALDEHYDES - EVIDENCE FOR A [1-((TRIALKYLSILYL)OXY)ALLYL]NICKEL(II) MECHANISM [J].

GRISSO, BA ;

JOHNSON, JR ;

MACKENZIE, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5160-5165

[6] Palladium-catalyzed coupling of allylic cyclic carbonates with aryl- and vinylstannanes in aqueous medium [J].

Kang, SK ;

Yamaguchi, T ;

Kim, JS ;

Choi, SC .

SYNTHETIC COMMUNICATIONS, 1997, 27 (07) :1267-1271

[7] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .28. ASYMMETRIC TOTAL SYNTHESES OF (-)-STRYCHNINE AND (+)-STRYCHNINE AND THE WIELAND-GUMLICH ALDEHYDE [J].

KNIGHT, SD ;

OVERMAN, LE ;

PAIRAUDEAU, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5776-5788

[8] A new approach to (+)-brefeldin A via a nickel-catalyzed coupling reaction of cyclopentenyl acetate and lithium 2-furylborate [J].

Kobayashi, Y ;

Watatani, K ;

Kikori, Y ;

Mizojiri, R .

TETRAHEDRON LETTERS, 1996, 37 (34) :6125-6128

[9] Nickel-catalyzed coupling reaction of 1,3-disubstituted secondary allylic carbonates and lithium aryl- and alkenylborates [J].

Kobayashi, Y ;

Mizojiri, R ;

Ikeda, E .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5391-5399

[10] SYNTHESIS OF ALLYLIC ALCOHOLS VIA PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLIC EPOXIDES AND ARYL OR VINYLIC HALIDES AND TRIFLATES [J].

LAROCK, RC ;

DING, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :804-806