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
Full Text: HTML
Citation Number: 0
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.
Related Articles:
[Xiong, Lu; Bi, Ming-Gang; Wu, Song; Tong, Yuan-Feng Journal of Asian Natural Products Research, 2012 , vol. 14, # 4 p. 322 - 326]
[Bezerra-Netto, Heleno J.C.; Lacerda, Daniel I.; Miranda, Ana Luisa P.; Alves, Helio M.; Barreiro, Eliezer J.; Fraga, Carlos A.M. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 23 p. 7924 - 7935]