Syntheses of 2,5-disubstituted dihydrofurans from γ-substituted chiral allenamides

被引：43

作者：

Berry, CR ^{[1
]}

Hsung, RP ^{[1
]}

Antoline, JE ^{[1
]}

Petersen, ME ^{[1
]}

Challeppan, R ^{[1
]}

Nielson, JA ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo0503411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Details of a synthesis of dihydrofurans using gamma-substituted chiral allenamides are described here. Some transformations of these dihydrofurans are also examined including a highly stereoselective dihydroxylation and a rare account of a Lewis acid-mediated removal of an N-acyl substituent at the anomeric carbon of a tetrahydrofuran ring system. These studies provide further support for the synthetic utility of allenamides.

引用

收藏

页码：4038 / 4042

页数：5

相关论文

共 67 条

[1] Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes [J].

Achmatowicz, M ;

Hegedus, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2229-2234

[2] New regio and stereoselective intermolecular Pauson-Khand reactions of allenamides [J].

Anorbe, L ;

Poblador, A ;

Domínguez, G ;

Pérez-Castells, J .

TETRAHEDRON LETTERS, 2004, 45 (23) :4441-4444

[3] Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds [J].

Antonioletti, R ;

Malancona, S ;

Bovicelli, P .

TETRAHEDRON, 2002, 58 (43) :8825-8831

[4] Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine:: synthesis of N-allenylsulfenimides [J].

Armstrong, A ;

Cooke, RS ;

Shanahan, SE .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3142-3143

[5] Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl Sulfides with tert-butoxycarbonyl azide.: Access to N-allenylsulfenimides [J].

Bacci, JP ;

Greenman, KL ;

Van Vranken, DL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4955-4958

[6] Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides [J].

Berry, CR ;

Hsung, RP .

TETRAHEDRON, 2004, 60 (35) :7629-7636

[7]

Berry CR, 2003, SYNLETT, P791

[8] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[9]

CARRIDO JL, 1998, J ORG CHEM, V69, P9406

[10]

CLOSE WJ, 1950, J ORG CHEM, V15, P1131

← 1 2 3 4 5 6 7 →