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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 

Stereocontrol in the EtAlCl(2)-induced cyclization of chiral gamma,delta-unsaturated methyl ketones to form cyclopentanones.

EtAlCl(2)-induced cyclization of chiral gamma,delta-unsaturated ketones 11c and 17b takes place mainly from the expected face. The selectivity is modest for 11c (60:40) in which the large substituent is a primary alkyl group and the medium substituent is a methyl group and excellent for 17b (93:7) in which the large substituent is a cyclohexyl group and the medium substituent is a methyl group. The cyclization of 17a is anomalous, suggesting that the phenyl group has more than a simple steric effect.[1]

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