Intermolecular C–H functionalization versus cyclopropanation of electron rich 1,1-disubstituted and trisubstituted alkenes

Autor:	Huw M. L. Davies, Zhanjie Li, Michael G. Coleman, Dominic L. Ventura
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Cyclopropanation Alkene Organic Chemistry Regioselectivity chemistry.chemical_element Vinyl ether Biochemistry Rhodium Cyclopropane Catalysis chemistry.chemical_compound chemistry Drug Discovery medicine Organic chemistry Enantiomeric excess medicine.drug
Zdroj:	Tetrahedron. 65:3052-3061
ISSN:	0040-4020
DOI:	10.1016/j.tet.2008.11.059
Popis:	Rhodium(II)-catalyzed reactions of aryldiazoacetates with electron rich 1,1-disubstituted and trisubstituted alkenes were systematically studied. The regio-, diastereo- and enantioselectivity of the chemistry was profoundly influenced by the nature of the substrates and the catalyst. Conditions were developed for either selective cyclopropanation or C–H insertion. Both reactions can be achieved with high diastereo- and enantioselectivity (for C–H insertion: >90% de, up to 96% ee, for cyclopropanation: >94% de, up to 95% ee). For the 1,1-disubstituted vinyl ethers, cyclopropanation occurs with variable diastereoselectivity but in optimized systems the cyclopropane is formed in >94% de and up to 98% ee.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::98055149ba4b959a815941203f7c14ef https://doi.org/10.1016/j.tet.2008.11.059 Zobrazit plný text záznamu Full Text from ScienceDirect