Photoinduced electron transfer-initiated asymmetric cyclization of N-benzoyl-α-dehydronaphthylalanine alkyl esters carrying chiral and bulky auxiliaries

Autor:	Taisuke Matsumoto, Kei Maekawa, Tetsutaro Igarashi, Kanji Kubo, Haruo Watanabe, Tadamitsu Sakurai, Yuji Sasaki
Rok vydání:	2007
Předmět:	chemistry.chemical_classification Chiral auxiliary Stereochemistry Organic Chemistry Diastereomer Biochemistry Medicinal chemistry Asymmetric induction Photoinduced electron transfer Solvent chemistry.chemical_compound Electron transfer chemistry Drug Discovery Methanol Alkyl
Zdroj:	Tetrahedron Letters. 48:4765-4770
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2007.04.134
Popis:	The irradiation of the title compounds [( Z )- 1 ] having ( S )-(+)- sec -butyl, (−)-mentyl and related chiral auxiliaries in methanol and 1,2-dichloroethane containing 2-(diethylamino)ethanol afforded chiral auxiliary-substituted (4 S ,5 S )-, (4 R ,5 R )-, (4 R ,5 S )- and (4 S ,5 R )-4,5-dihydrooxazole derivatives ( 2 ) along with ( E )- 1 . It was found that the photoinduced electron transfer-initiated cyclization of 1 gives either of the two diastereomers for cis - 2 and trans - 2 in diastereomeric excess whose value varies from 6% to 81% depending on solvent and chiral auxiliary.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f5d47bca7ec1392deb911652ef22ff61 https://doi.org/10.1016/j.tetlet.2007.04.134 Zobrazit plný text záznamu Full Text from ScienceDirect