Diastereoselective Synthesis of Complex cis-Hexahydroindanes by Reductive Alkylation
…, VL Rendina, JS Kingsbury
Index: Kaplan, Hilan Z.; Rendina, Victor L.; Kingsbury, Jason S. Journal of Organic Chemistry, 2013 , vol. 78, # 9 p. 4620 - 4626
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Abstract
An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The reaction is convergent, completely diastereoselective, and shows a broad scope with regard to the electrophile.
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