A facile diastereoselective synthesis of functionalized 1,2,3-trisubstituted benzocyclopentenes through the cycloaddition of bis(phenylsulfonyl)iodonium ylides to cyclic alkenes

被引：19

作者：

Adam, W

Gogonas, EP

Hadjiarapoglou, LP ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, Sect Organ Chem & Biochem, GR-45110 Ioannina, Greece

[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期

关键词：

D O I：

10.1021/jo035362e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thermal cycloaddition of beta-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo[3.3.0] octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.

引用

收藏

页码：9155 / 9158

页数：4

相关论文

共 16 条

[1]

Adam W, 2003, SYNLETT, P1165

[2] Bis(sulfonyl)methyl insertion into alkenyl versus phenyl carbon-hydrogen bonds in the reaction of bis(sulfonyl)iodonium ylides with highly phenylated ethylenes [J].

Adam, W ;

Gogonas, EP ;

Hadjiarapoglou, LP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (06) :1064-1068

[3] A stereoselective and regioselective synthesis of trans,trans-configured 1,2,3-trisubstituted indanes:: Cycloaddition of alkenes with iodonium ylides of β-disulfones [J].

Adam, W ;

Bosio, SG ;

Gogonas, EP ;

Hadjiarapoglou, LP .

SYNTHESIS-STUTTGART, 2002, (14) :2084-2090

[4] ELECTROPHILIC AND HOMOLYTIC CLEAVAGE OF 5-ARYL-5H-DIBENZIODOLES [J].

BERINGER, FM ;

CHANG, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (26) :4055-&

[5] PHENYLIODONIUM BIS(PHENYLSULFONYL)METHYLIDE - A NEW HYPERVALENT IODONIUM YLIDE [J].

HADJIARAPOGLOU, L ;

SPYROUDIS, S ;

VARVOGLIS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7178-7179

[6] REACTIVITY OF PHENYLIODONIUM BIS(ARYLSULFONYL)METHYLIDES TOWARDS ALKENES AND ALKYNES - CRYSTAL-STRUCTURE OF 9-PHENYLSULPHONYL-1,2,3,4,4A,9A-HEXAHYDRO-1,4-METHANOFLUORENE [J].

HATJIARAPOGLOU, L ;

VARVOGLIS, A ;

ALCOCK, NW ;

PIKE, GA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10) :2839-2846

[7] REARRANGEMENT OF BENZYLICALLY LITHIATED METHYLARYL ALKYL SULFONES [J].

MADAJ, EJ ;

SNYDER, DM ;

TRUCE, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3466-3469

[8] Synthesis of polyquinane natural products: An update [J].

Mehta, G ;

Srikrishna, A .

CHEMICAL REVIEWS, 1997, 97 (03) :671-719

[9] ORGANIC-PHOTOCHEMISTRY .50. PHOTOINDUCED SKELETAL REARRANGEMENT OF ALKYLINDENES [J].

MORRISON, H ;

GIACHERIO, D ;

PALENSKY, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) :1051-1058

[10] ROLE OF NONBONDING ORBITALS, S MIXING, AND D-ORBITAL PARTICIPATION IN HYPERVALENT MOLECULES [J].

MUSHER, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (04) :1370-&