Stereocontrol in the EtAlCl2-Induced Cyclization of Chiral γ,δ-Unsaturated Methyl Ketones To Form Cyclopentanones

Autor:	Barry B. Snider, Tracy P. Marien, Mercedes Lobera
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Magnetic Resonance Spectroscopy Ketone Organic Chemistry Substituent Cyclopentanes Ketones Chemical synthesis chemistry.chemical_compound chemistry Cyclization Organometallic Compounds Organic chemistry Indicators and Reagents Stereoselectivity Selectivity
Zdroj:	The Journal of Organic Chemistry. 68:6451-6454
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo034561v
Popis:	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.
Databáze:	OpenAIRE
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