Enantioselective Synthesis of Substituted Indanones

Significance

Chiral indane and indanone motifs can be found in many biologically active compounds; a number of asymmetric approaches towards the indane scaffold have been developed. In this paper the authors considered a formal [3+2] construction of these compounds, representing a novel modular synthetic strategy. Thus, the desired products are obtained in a microwave-assisted Heck cyclization of enantioenriched halo-substituted allylic alcohols, which can be obtained via carbonyl-ene reaction of aldehydes with silyl­oxyallenes; the latter could be easily prepared from acylsilanes and terminal alkenes. Under optimized conditions Heck cyclization proceeds with high levels of chirality transfer; a range of products was obtained with 70-92% yields and 75-90% ee.