Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols

Autor:	Rachid Baati, Sylvie Goncalves, Philippe Maillos, Marc Nicolas
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Ketone Organic Chemistry Cationic polymerization Epoxide Total synthesis Biochemistry Combinatorial chemistry Chemical synthesis chemistry.chemical_compound chemistry Drug Discovery Tetrachloride Organic chemistry Chemoselectivity Enantiomeric excess
Zdroj:	Tetrahedron. 67:8373-8382
ISSN:	0040-4020
DOI:	10.1016/j.tet.2011.08.050
Popis:	10-Methyl-cis-9-decalinols are important motifs in several natural products and key intermediates in total synthesis. Herein, we wish to describe a highly chemo- and diastereoselective cyclization of keto-epoxides leading to 10-methyl-cis-9-decalinols. This method based on the use of zirconium(IV) tetrachloride permits the access to a wide variety of cis-decalinols in good to excellent yields. The cationic cyclization could also be performed with chiral keto-epoxide with complete control of the diastereoselectivity affording cis-bicyclic tertiary alcohol with good enantiomeric excess. The chemo- and the diastereoselectivity are assumed to result from the ability of Zr(IV) to generate highly stable bidentic complexes with α-hydroxy-ketone intermediates.
Databáze:	OpenAIRE
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