Ceric(IV)-mediated reaction of methylenecyclopropanes in organic synthesis: A facile access to dihydrofurans and cyclobutanones

被引：31

作者：

Chen, WL

Huang, M

Zhou, HW

Ren, LJ

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

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

来源：

SYNTHESIS-STUTTGART | 2006年 / 04期

关键词：

methylenecyclopropanes; ammonium cerium(IV) nitrate; 1,3-dicarbonyl compounds; dihydrofuran; cyclobutanone;

D O I：

10.1055/s-2006-926298

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylidenecyclopropanes undergo CAN-mediated addition reactions with 1,3-dicarbonyl compounds or ring rearrangement reactions leading to dihydrofuran and cyclobutanone derivatives, respectively, in moderate yields.

引用

页码：609 / 614

页数：6

共 74 条

[1]

AUE DH, 1973, TETRAHEDRON LETT, P4799

[2]

Bernard AM, 1998, SYNLETT, P668

[3]

BINGER P, 1987, TOP CURR CHEM, V135, P77

[4] Diastereoselective SmI2-mediated cascade radical cyclisations of methylenecyclopropane derivatives -: a synthesis of paeonilactone B [J].

Boffey, RJ ;

Santagostino, M ;

Whittingham, WG ;

Kilburn, JD .

CHEMICAL COMMUNICATIONS, 1998, (17) :1875-1876

[5] Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives -: syntheses of paeonilactone B and 6-epi-paeonilactone A [J].

Boffey, RJ ;

Whittingham, WG ;

Kilburn, JD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (05) :487-496

[6]

BOWRY VW, 1990, CHEM COMMUN, P92

[7] Synthesis of methylene- and alkylidenecyclopropane derivatives [J].

Brandi, A ;

Goti, A .

CHEMICAL REVIEWS, 1998, 98 (02) :589-635

[8] Heterocycles from alkylidenecyclopropanes [J].

Brandi, A ;

Cicchi, S ;

Cordero, FM ;

Goti, A .

CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269

[9] Palladium-catalyzed addition of ketones to alkylidenecyclopropanes [J].

Camacho, DH ;

Nakamura, I ;

Oh, BH ;

Saito, S ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 2002, 43 (16) :2903-2907

[10] Palladium-catalyzed addition of alcohol pronucleophiles to alkylidenecyclopropanes [J].

Camacho, DH ;

Nakamura, I ;

Saito, S ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :270-275

← 1 2 3 4 5 6 7 8 →