PdCl2/NaI-catalyzed homodimeric coupling-cyclization reaction of 2,3-allenols:: An efficient synthesis of 4-(1',3'-dien-2'-yl)-2,5-dihydrofuran derivatives

被引：51

作者：

Deng, Youqian ^{[1
]}

Yu, Yihua ^{[2
]}

Ma, Shengming ^{[1
,3
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Peoples R China

[2] E China Normal Univ, Dept Phys, Shanghai Key Lab Funct Magnet Resonance Imaging, Shanghai 200062, Peoples R China

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 02期

关键词：

D O I：

10.1021/jo702332m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A PdCl2/NaI-catalyzed homodimeric coupling-cyclization reaction of 2,3-allenols was observed to provide an efficient route to 4-(1',3'-dien-2'-yl)-2,5-dihydrofuran derivatives. By using the easily available optically active starting materials, 2,5-dihydrofurans with high enantiopurity may be prepared. A Pd(II) catalyzed mechanism was also discussed.

引用

页码：585 / 589

页数：5

共 82 条

[31] SYNTHESIS AND REACTIONS OF LITHIO DERIVATIVES OF 1-ALLENYLBENZOTRIAZOLE [J].

KATRITZKY, AR ;

VERIN, SV .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) :323-328

[32] Synthesis of conjugated dienes from vinyl epoxides, vinyl acetonides and 2,5-dihydrofurans via zirconocene-mediated deoxygenation [J].

Kim, S ;

Kim, KH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (08) :1095-1097

[33] Strikingly simple direct α-allylation of aldehydes with allyl alcohols:: Remarkable advance in the Tsuji-Trost reaction [J].

Kimura, M ;

Horino, Y ;

Mukai, R ;

Tanaka, S ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10401-10402

[34]

Krause N., 2004, MODERN ALLENE CHEM, V1

[35] TUMOR INHIBITORS .86. ISOLATION AND STRUCTURAL ELUCIDATION OF LIATRIN, A NOVEL ANTILEUKEMIC SESQUITERPENE LACTONE FROM LIATRIS-CHAPMANII [J].

KUPCHAN, SM ;

DAVIES, VH ;

FUJITA, T ;

COX, MR ;

RESTIVO, RJ ;

BRYAN, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (10) :1853-1858

[36]

LANDOR SR, 1982, CHEM ALLENES, V1

[37] Palladium-catalyzed annulation [J].

Larock, RC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :111-124

[38] PdII-catalyzed oxidative dimeric cyclization-coupling reaction of 2,3-allenoic acids:: An efficient synthesis of bibutenolide derivatives [J].

Ma, SM ;

Yu, ZQ ;

Gu, ZH .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2351-2356

[39]

Ma SM, 2005, TOP ORGANOMETAL CHEM, V14, P183

[40] PdCl2-catalyzed two-component cross-coupling cyclization of 2,3-allenoic acids with 2,3-allenols.: An efficient synthesis of 4-(1′,3′-dien-2′-yl)-2(5H)-furanone derivatives [J].

Ma, SM ;

Gu, ZH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6182-6183

← 1 2 3 4 5 6 7 8 9 →