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

被引：7

作者：

Araujo, N. ^{[1
]}

Gil, Maria V. ^{[1
]}

Roman, E. ^{[1
]}

Serrano, Jose A. ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2006年 / 15期

关键词：

nitroalkenes; furan; Diels-Alder reaction; high-pressure reaction; 7-oxabicyclo[2.2.1]heptenes;

D O I：

10.1055/s-2006-942454

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Diels-Alder reactions between furan and chiral (E)-1,2-dideoxy-1-nitroalkenes derived from D-mannose and D-galactose take place quantitatively at room temperature and under high pressure (13 kbar), thus yielding, in each case, mixtures of the four possible stereoisomers of 3-nitro-2-(penta-O-acetylpentitol-1-yl)-7-oxabicyclo[2.2.1]hept-5-enes. The 3-nitro- 7-oxabicyclo[2.2.1]hept-5-ene-2-carbaldehydes were obtained by deacetylation, followed by oxidative degration of the sugar chains of the corresponding major stereoisomers produced in each of the two Diels-Alder reactions.

引用

页码：2503 / 2506

页数：4

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