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- Title
Tandem Inter [4+2]/Intra [3+2] Cycloadditions of Nitroalkenes. Application to the Synthesis of Aminocarbasugars.
- Authors
Denmark, Scott E.; Juhl, Martin
- Abstract
The tandem inter [4+2]/intra [3+2] cycloaddition of nitroalkenes in the bridged mode was applied to the stereoselective synthesis of β- D-4-amino-2,4-dideoxycarbagulose, a representative aminocarbasugar. The synthesis required only five steps from known materials and delivered the protected aminocarbasugar (−)- 20 in excellent yield (see Scheme 9). The success of the synthetic sequence relies on 1) the ability to incorporate O-substituents at the nitroalkene moiety, 2) the identification of a suitably modified chiral dienophile, and in particular 3) the development of specific experimental conditions and protocols that allow for the formation and isolation of the highly sensitive nitroso acetals. The reduction of the C(1) carbonyl group of (+)- 19 gave unexpected stereoselectivity, which could be rationalized by a conformational inversion of the substrate (see Scheme 11).
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 11, p3712
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(200211)85:11<3712::AID-HLCA3712>3.0.CO;2-5