[2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

Autor:	Craig C. Humber, Jeffrey M. Manthorpe, Gordon L. Lange
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Steric effects Chiral auxiliary Double bond Stereochemistry Organic Chemistry Synthon Catalysis Cycloaddition Adduct Inorganic Chemistry chemistry.chemical_compound chemistry Cyclopentene Physical and Theoretical Chemistry Enantiomer
Zdroj:	Tetrahedron: Asymmetry. 13:1355-1362
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(02)00339-7
Popis:	Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the ‘masked’ double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative 13 C NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary on the synthon.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::40d4fb00f07e12ede0c80b264d010d13 https://doi.org/10.1016/s0957-4166(02)00339-7 Zobrazit plný text záznamu Full Text from ScienceDirect