Organocatalytic synthesis of multiple substituted bicyclo[4.4.0]decalin system
Shaik Anwar1, Hui-Ju Chang, Kwunmin Chen
1Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 116, ROC.
Abstract:
An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.
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