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

The Journal of organic chemistry (2003-08-05)
Barry B Snider, Mercedes Lobera, Tracy P Marien
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethylaluminum dichloride solution, 1.0 M in hexanes
Sigma-Aldrich
Ethylaluminum dichloride
Sigma-Aldrich
Ethylaluminum dichloride solution, 25 wt. % in toluene

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