351355-13-0Relevant academic research and scientific papers
Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via ( - )-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation
Laqua,Fr?hlich,Wibbeling,Hoppe
, p. 96 - 104 (2001)
By treatment of the racemic 3-(indenyl)alkyl carbamate rac-8 with sec-BuLi-( - )-sparteine, cyclocarbolithiation occurs, which is accompanied by kinetic resolution during the cyclisation step. After addition of electrophiles, the stereohomogeneous optically active benzobicyclo[3.3.0]octenols of type 13 are obtained. Increasing the temperature from -78 to -40°C or the application of TMEDA instead of ( - )-sparteine yields the formation of the tricyclic cyclopropane 14.
