Mesitylacetophenone derivatives

We turn next to a study in which it has been possible to pinpoint the factors responsible for asymmetric induction. The reaction in question is one that has been thoroughly investigated in solution by Wagner and coworkers—the photochemical conversion of achiral a-mesitylacetophenone derivatives into chiral cyclopentanols (Scheme 4) [15]. Following our usual protocol, we prepared the para-carboxylic acid derivative 9a and treated this with a series of optically pure... 

Cheung, E., Rademacher, K., Scheffer, J. R., and Trotter, J., An investigation of the solid state photochemistry of a-mesitylacetophenone derivatives asymmetric induction studies and crystal structure-reactivity relationships, Tetrahedron, 56, 6739, 2000. 

Solid-state photolysis of salt crystals of a-mesitylacetophenone-/ -carbox-ylic acid 55 and optically pure amines such as (S)-( — )-phenylethylamine or ( R,2S)-( —)-norephedrine caused 8-hydrogen abstraction from the methyl group, and then cyclization to produce the corresponding 2-indanol derivative 56 in excellent yield and high enantiomeric excess (Scheme 12) [68]. 

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