Mechanistic switch leading to highly efficient chirality transfer in Pd(0)-catalyzed coupling-cyclization of aryl iodides with 1:1 acid-base salts of 2,3-allenoic acids and L-(-)-cinchonidine or D-(+)-/L-(-)-α-methylbenzylamine.: Enantioselective synthesis of highly optically active 3-aryl polysubstituted butenolides

被引：52

作者：

Ma, SM ^{[1
]}

Shi, ZJ ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 05期

关键词：

D O I：

10.1039/b109645a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient methodology provides an easy access to highly optically active polysubstituted butenolides starting from aryl halides and 1:1 salts of optically active 2,3-allenoic acid-base via an oxidative addition-coordinative cyclization-reductive elimination mechanism, which led to the high efficiency of this chirality isomerization reaction.

引用

收藏

页码：540 / 541

页数：2

相关论文

共 32 条

[11]

LANDOR SR, 1982, CHEM ALLENES, V3, P587

[12] MERCURY IN ORGANIC-CHEMISTRY .12. SYNTHESIS OF BETA-CHLORO-DELTA-ALPHA-DELTA-BETA-BUTENOLIDES VIA MERCURATION-CARBONYLATION OF PROPARGYLIC ALCOHOLS [J].

LAROCK, RC ;

RIEFLING, B ;

FELLOWS, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :131-137

[13]

Lee G.C.M., 1991, PCT Int. Appl. WO 91 16,055, Patent No. [91 16,055, 9116055]

[14]

LEE GCM, 1990, Patent No. 372940

[15] Novel CuX2-mediated cyclization of acid-base salts of (L)-cinchonidine or (D)-/(L)-α-methylbenzylamine and 2,3-allenoic acids in an aqueous medium.: An efficient entry to optically active β-halobutenolides [J].

Ma, SM ;

Wu, SL .

CHEMICAL COMMUNICATIONS, 2001, (05) :441-442

[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] Pd(0)/Ag+-cocatalyzed cyclization reaction of 1,2-allenic carboxylic acids with aryl/alkenyl halides.: An efficient synthesis of butenolides [J].

Ma, SM ;

Shi, ZJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6387-6389

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