Unexpected reactions:: From (2S,3R)-2-(endo-D-Galacto-pentaacetoxypentyl)-1,4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene to chiral cyclic ethers

被引：6

作者：

Araujo, Noelia ^{[1
]}

Cumbrera, Francisco L. ^{[2
]}

Gil, Maria V. ^{[1
]}

Ortiz, Angel L. ^{[3
]}

Roman, Emilio ^{[1
]}

Serrano, Jose A. ^{[1
]}

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ & Inorgan, E-06071 Badajoz, Spain

[2] Univ Extremadura, Fac Ciencias, Dept Fis, E-06071 Badajoz, Spain

[3] Univ Extremadura, Escuela Ingn Ind, Dept Ingn Mecan Energet & Mat, E-06071 Badajoz, Spain

来源：

SYNLETT | 2008年 / 05期

关键词：

asymmetric synthesis; carbohydrate nitroalkenes; Diels-Alder reaction; heterocycles; ring opening;

D O I：

10.1055/s-2008-1042798

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The high-pressure Diels-Alder reaction between 2,5-dimethylfuran and D-galacto-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitrohept-1-enitol led, after fractional crystallization from the crude product, to pure (2S,3R)-2-(endo-D-galacto-pentaacetoxypentyl)-1,4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene. The structure was determined through a chemical route and by X-ray powder diffractometry. De-acetylation of the sugar side chain of this adduct caused the ring opening of the bicyclic system, followed by a tandem process of intramolecular nucleophilic additions, thus leading to new chiral bicyclic and tricyclic ethers.

引用

页码：687 / 690

页数：4

共 21 条

[1] Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-alpha-sulfinylacrylates [J].

Adrio, J ;

Carretero, JC ;

Ruano, JLG ;

Cabrejas, LMM .

TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1623-1631

[2] New molecular scaffolds:: Synthesis of (2R,3R)- and (2S,3S)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carbaldehyde from furan [J].

Araujo, N. ;

Gil, Maria V. ;

Roman, E. ;

Serrano, Jose A. .

SYNTHESIS-STUTTGART, 2006, (15) :2503-2506

[3] REACTION OF 1,1,1-TRICHLORO-3-NITRO-2-PROPENE WITH FURANS - A REEXAMINATION [J].

BALTHAZOR, TM ;

GAEDE, B ;

KORTE, DE ;

SHIEH, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4547-4549

[4] ON THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF FURAN - REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENOLS AND CYCLOHEXADIENOLS [J].

BRION, F .

TETRAHEDRON LETTERS, 1982, 23 (50) :5299-5302

[5] Asymmetric synthesis of the putative structure of (-)-oryzoxymycin [J].

Bunnage, ME ;

Ganesh, T ;

Masesane, IB ;

Orton, D ;

Steel, PG .

ORGANIC LETTERS, 2003, 5 (03) :239-242

[6] Synthesis and applications of (1R, 5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions [J].

Burke, MJ ;

Allan, MM ;

Parvez, M ;

Keay, BA .

TETRAHEDRON-ASYMMETRY, 2000, 11 (13) :2733-2739

[7] Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes [J].

Crowley, PJ ;

Fawcett, J ;

Kariuki, BM ;

Moralee, AC ;

Percy, JM ;

Salafia, V .

ORGANIC LETTERS, 2002, 4 (23) :4125-4128

[8] ORGANIC REACTIONS AT HIGH-PRESSURE - CYCLOADDITIONS WITH FURANS [J].

DAUBEN, WG ;

KRABBENHOFT, HO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) :1992-1993

[9] Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid [J].

Evans, DA ;

Barnes, DM .

TETRAHEDRON LETTERS, 1997, 38 (01) :57-58

[10] First asymmetric Diels-Alder reactions of furan and chiral acrylates. Usefulness of acid heterogenous catalysts [J].

Fraile, JM ;

Garcia, JI ;

Gracia, D ;

Mayoral, JA ;

Pires, E .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9479-9482

← 1 2 3 →