Reverse of regioselectivity in intramolecular nucleophilic substitution of π-allyl palladium species.: Highly selective formation of vinylic cyclopropanes via the pd(0) catalyzed coupling-cyclization reaction of organic iodides with 2-(2′,3′-dienyl)malonates

被引：63

作者：

Ma, SM ^{[1
]}

Zhao, SM ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol006165u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Vinylic cyclopropanes were formed highly selectively via the Pd(PPh3)(4)-catalyzed insertion-intramolecular nucleophilic substitution reaction of aryl or 1-alkenyl iodides with 2-(2',3'-dienyl)malonates. The regioselectivity observed here is different from what was reported by Cazes et al.

引用

页码：2495 / 2497

页数：3

共 31 条

[11]

JEFFERY T, 1987, SYNTHESIS-STUTTGART, P70

[12] Novel synthesis of 4-oxo-1-isoquinolone derivatives utilizing inter- and intramolecular tandem carbopalladation-heterocyclic ring expansion [J].

Jeong, IY ;

Nagao, Y .

TETRAHEDRON LETTERS, 1998, 39 (47) :8677-8680

[13] ENANTIOSELECTIVE, PALLADIUM-CATALYZED HETEROANNULATION AND CARBOANNULATION OF ALLENES USING FUNCTIONALLY-SUBSTITUTED ARYL AND VINYLIC IODIDES [J].

LAROCK, RC ;

ZENNER, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :482-483

[14] REGIOSELECTIVE, PALLADIUM-CATALYZED HETEROANNULATION AND CARBOANNULATION OF 1,2-DIENES USING FUNCTIONALLY SUBSTITUTED ARYL HALIDES [J].

LAROCK, RC ;

BERRIOSPENA, NG ;

FRIED, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2615-2617

[15] Palladium(0)-catalyzed cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. A facile solid-phase synthesis of butenolides [J].

Ma, SM ;

Duan, DH ;

Shi, ZJ .

ORGANIC LETTERS, 2000, 2 (10) :1419-1422

[16] Synthesis of β-halobutenolides and their Pd(0)-catalyzed cross-coupling reactions with terminal alkynes and organozinc reagents.: A general route to β-substituted butenolides and formal synthesis of cis-whisky lactone [J].

Ma, SM ;

Shi, ZJ ;

Yu, ZQ .

TETRAHEDRON, 1999, 55 (41) :12137-12148

[17] CuX2-mediated cyclization reaction of 2,3-allenoic acids.: An efficient route to β-halobutenolides [J].

Ma, SM ;

Wu, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9314-9317

[18] Palladium-catalyzed cyclization reaction of allylic bromides with 1,2-dienyl ketones. An efficient synthesis of 3-allylic polysubstituted furans [J].

Ma, SM ;

Li, LT .

ORGANIC LETTERS, 2000, 2 (07) :941-944

[19] Synthesis of β-halobutenolides and their Pd(0)/CuI-catalyzed cross-coupling reactions with terminal alkynes.: A general route to β-(1′-alkynyl)butenolides [J].

Ma, SM ;

Shi, ZJ ;

Yu, ZQ .

TETRAHEDRON LETTERS, 1999, 40 (12) :2393-2396

[20] FACILE FORMATION OF 7-MEMBERED AND 8-MEMBERED CYCLOALKENES VIA CATALYTIC AND CYCLIC CARBOPALLADATION OF ALLENES [J].

MA, SM ;

NEGISHI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4730-4732

← 1 2 3 4 →