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  • Organocatalytic synthesis of multiple substituted bicyclo[4.4.0]decalin system.

Organocatalytic synthesis of multiple substituted bicyclo[4.4.0]decalin system.

Organic letters (2011-04-12)
Shaik Anwar, Hui-Ju Chang, Kwunmin Chen
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%
Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%