Six-Membered Cyclic Nitronates as 1,3-Dipoles in Formal [3+3]-Cycloaddition with Donor-Acceptor Cyclopropanes. Synthesis of New Type of Bicyclic Nitrosoacetals

被引：67

作者：

Gorbacheva, Evgenia O. ^{[1
,2
]}

Tabolin, Andrey A. ^{[1
]}

Novikov, Roman A. ^{[1
]}

Khomutova, Yulia A. ^{[1
]}

Nelyubina, Yulia V. ^{[3
]}

Tomilov, Yury V. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Moscow 125047, Russia

[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

DIVERSITY-ORIENTED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITION; 3+2 ANNULATION; TANDEM INTER; NITROALKENES; TETRAHYDRO-1,2-OXAZINES; AMINOCYCLOPROPANES; ALDEHYDES;

D O I：

10.1021/ol303292c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first formal [3 + 3]-cycloaddition of nitronates with donor-acceptor cyclopropanes is reported. The reaction is catalyzed by ytterbium trifluoromethanesulfonate and leads to hitherto unknown bicyclic nitrosoacetals, possessing two annelated six-membered rings.

引用

页码：350 / 353

页数：4

共 50 条

[31] Enantiospecific Sn(II)- and Sn(IV)-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes [J].

Pohlhaus, PD ;

Johnson, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16014-16015

[32] Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers [J].

Qi, Xiangbing ;

Ready, Joseph M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) :7068-7070

[33] Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis [J].

Reissig, HU ;

Zimmer, R .

CHEMICAL REVIEWS, 2003, 103 (04) :1151-1196

[34]

Righi P, 1998, CHEM-EUR J, V4, P2501, DOI 10.1002/(SICI)1521-3765(19981204)4:12<2501::AID-CHEM2501>3.3.CO

[35]

2-9

[36] The cycloaddition of nitrones with homochiral cyclopropanes [J].

Sapeta, Katarina ;

Kerr, Michael A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8597-8599

[37] Synthesis of Cyclohexanes via [3+3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes [J].

Sapeta, Katarina ;

Kerr, Michael A. .

ORGANIC LETTERS, 2009, 11 (10) :2081-2084

[38] STERIC STRUCTURE OF 6R-8R'-2,9-DIOXA-1-AZABICYCLO[4.3.0]NONANE DERIVATIVES [J].

SHITKIN, VM ;

CHLENOV, IE ;

TARTAKOVSKII, VA .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1977, 26 (01) :187-189

[39] SPATIAL STRUCTURE OF 8-SUBSTITUTED 6-METHYL-2,9-DIOXA-1-AZA-BICYCLO[4.3.0]NONANE DERIVATIVES [J].

SHITKIN, VM ;

KHUDAK, VI ;

CHLENOV, IE ;

TARTAKOVSKII, VA .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1974, 23 (08) :1836-1838

[40] Enantioselective addition of nitrones to activated cyclopropanes [J].

Sibi, MP ;

Ma, ZH ;

Jasperse, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5764-5765

← 1 2 3 4 5 →