✦ LIBER ✦
ChemInform Abstract: Enantiospecific Preparation of gem-Dimethylcyclopropane Fused Cycloheptanes via Valence Tautomerization of 3,4-Homotropilidene under Thermodynamic and Kinetic Control.
✍ Scribed by T. SUGIMURA; T. FUTAGAWA; T. KATAGIRI; N. NISHIYAMA; A. TAI
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Enantiospecific Preparation of gem-Dimethylcyclopropane Fused Cycloheptanes via Valence Tautomerization of 3,4-Homotropilidene under Thermodynamic and Kinetic Control. -Regioselective addition of dichlorocarbene to the 4-alkoxy-8,8-dimethylcycloheptatriene (I) followed by a reductive rearrangement provides an entry to the 3,4-homotropylidene derivatives (IV), (V), and (VI). Using chiral alkoxysubstituted educts such as (VII), the stereospecificity of the rearrangement allows the preparation of optically active products (XII) and (XIII).