Rh(II)-catalyzed Sommelet-Hauser rearrangement

被引：52

作者：

Liao, Mingyi

Peng, Lingling

Wang, Jianbo ^{[1
]}

机构：

[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol703058p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic Sommelet-Hauser rearrangement is reported. The Rh(II)-catalyzed reaction of aryldiazoacetates with ethyl benzylthioacetate affords Sommelet-Hauser rearrangement products in good to excellent yields. This reaction provides a reliable and efficient way to introduce a substituent to the ortho position of arylacetates.

引用

收藏

页码：693 / 696

页数：4

相关论文

共 51 条

[1] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[2] Catalytic cyclopropanation of electron deficient alkenes mediated by chiral and achiral sulfides: scope and limitations in reactions involving phenyldiazomethane and ethyl diazoacetate [J].

Aggarwal, VK ;

Smith, HW ;

Hynd, G ;

Jones, RVH ;

Fieldhouse, R ;

Spey, SE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3267-3276

[3]

Beall LS, 1998, ADV NITROG HETERCYC, V3, P117

[4] Stereoselectivity of the thia-Sommelet [2,3]-dearomatization [J].

Berger, R ;

Ziller, JW ;

Van Vranken, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :841-842

[5]

Clark J.S., 2002, NITROGEN OXYGEN SULF, P1

[6] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].

Davies, HML ;

Bruzinski, PR ;

Lake, DH ;

Kong, N ;

Fall, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907

[7] ENANTIOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES BY RHODIUM(II) CATALYZED DECOMPOSITION OF VINYLDIAZOMETHANES IN THE PRESENCE OF ALKENES [J].

DAVIES, HML ;

HUTCHESON, DK .

TETRAHEDRON LETTERS, 1993, 34 (45) :7243-7246

[8] Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].

Davies, HML ;

Bruzinski, PR ;

Fall, MJ .

TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136

[9]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[10] Recent advances in asymmetric catalytic metal carbene transformations [J].

Doyle, MP ;

Forbes, DC .

CHEMICAL REVIEWS, 1998, 98 (02) :911-935

← 1 2 3 4 5 6 →