Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines

被引：18

作者：

Egart, Boris ^{[1
]}

Lentz, Dieter ^{[1
]}

Czekelius, Constantin ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

关键词：

ORGANOSELENIUM-INDUCED CYCLIZATION; SELENIUM-INDUCED CYCLIZATION; INDUCED STEREOSELECTIVE CYCLIZATION; OPTICALLY-ACTIVE ISOXAZOLIDINES; ONE-POT SYNTHESIS; ELECTROPHILIC CYCLIZATION; CYCLOADDITION REACTIONS; CONVENIENT SYNTHESIS; SYNTHETIC ROUTE; BETA;

D O I：

10.1021/jo3026725

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular bromoamination of O-allyl-N-tosyl-hydroxylamines results in the formation of isoxazolidines via selective 5-endo-tet cyclization. This process occurs trans-selectively in high yield and diastereoselectivity. The obtained bromo-isoxazolidines provide access to other useful building blocks, such as 2-azido-aminoalcohols, diaminoalcohols, and aziridines.

引用

页码：2490 / 2499

页数：10

共 80 条

[1] HALOCYCLIZATIONS - THE CYCLIZATION OF HETEROCYCLIC OLEFINIC AMIDES AND UREAS [J].

BALKO, TW ;

BRINKMEYER, RS ;

TERANDO, NH .

TETRAHEDRON LETTERS, 1989, 30 (16) :2045-2048

[2] Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine [J].

Bates, Roderick W. ;

Nemeth, Joseph A. ;

Snell, Robert H. .

SYNTHESIS-STUTTGART, 2008, (07) :1033-1038

[3] Synthesis of (-)-Sedinine by Allene Cyclization and Iminium Ion Chemistry [J].

Bates, Roderick W. ;

Lu, Yongna .

ORGANIC LETTERS, 2010, 12 (17) :3938-3941

[4] O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization [J].

Bates, RW ;

Sa-Ei, K .

ORGANIC LETTERS, 2002, 4 (24) :4225-4227

[5] 2-OXAZOLINES (4,5-DIHDRO-OXAZOLES) BY ORGANOSELENIUM-INDUCED CYCLIZATION OF ALLYLIC UREAS [J].

BETANCOR, C ;

LEON, EI ;

PRANGE, T ;

SALAZAR, JA ;

SUAREZ, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) :450-452

[6] A NEW BETA-LACTAM SYNTHESIS [J].

BILOSKI, AJ ;

WOOD, RD ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3233-3235

[7] Reserpine: A challenge for total synthesis of natural products [J].

Chen, FE ;

Huang, J .

CHEMICAL REVIEWS, 2005, 105 (12) :4671-4706

[8] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A ;

GUARNA, A ;

DESARLO, F .

TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354

[9] SELENIUM INDUCED STEREOSELECTIVE CYCLIZATION OF N-PROTECTED 3-HYDROXY-4-PENTENYLAMINES [J].

COOPER, MA ;

WARD, AD .

TETRAHEDRON LETTERS, 1992, 33 (40) :5999-6002

[10] SYNTHESIS OF FUNCTIONALIZED PYRROLIDINES FROM N(BENZYLIDENE)-HOMOALLYL AMINES AND N-(ALKYLIDENE)-HOMOALLYLAMINES [J].

DESMAELE, D ;

DEKIMPE, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (19) :2029-2030

← 1 2 3 4 5 6 7 8 →