Catalytic asymmetric synthesis of nitrocyclopropane carboxylates

Autor:	André B. Charette, Vincent N. G. Lindsay, Dino Alberico, Benoît Moreau
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Cyclopropanation Organic Chemistry Hypervalent molecule Enantioselective synthesis Biochemistry Medicinal chemistry Cyclopropane Catalysis chemistry.chemical_compound chemistry Ylide Drug Discovery Nitro Cis–trans isomerism
Zdroj:	Tetrahedron. 68:3487-3496
ISSN:	0040-4020
Popis:	A Cu(I)-catalyzed asymmetric cyclopropanation of alkenes with an iodonium ylide has been developed. The copper source, hypervalent iodine source, solvent, and additives all have a significant effect on the yields and enantioselectivities. High enantioselectivity (up to 99:1 er) and diastereoselectivity (95:5 dr trans/cis) were achieved for a wide range of alkenes. Conditions were developed to convert the trans products to the cis isomers. In addition, 1-nitrocyclopropyl carboxylates were transformed into the corresponding substituted cyclopropane amino acids and aminocyclopropanes. Moreover, a comparative study between Zn- and In-mediated reduction reactions of the nitro group in these compounds with regards to the er erosion in the process is also documented.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4a052ca06e29db2369ecbd7b54b0f77f https://doi.org/10.1016/j.tet.2011.05.113 Zobrazit plný text záznamu Full Text from ScienceDirect