Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: stereoselective routes to α- and β-amino acids

Autor:	Dong-Ho Kang, Sung-Kee Chung, Tae-Heum Jeong
Rok vydání:	1998
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Stereochemistry Moiety Stereoselectivity Ring (chemistry) Enone Amino acid
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :969-976
ISSN:	1364-5463 0300-922X
DOI:	10.1039/a705390h
Popis:	Organoselenium-induced cyclofunctionalization of the (S)-N-(α,β-unsaturated) acylprolinamides 1, 7 and 14 has been found to produce the 7-membered bislactam products 2 and 15, or the 6-membered phenylselenolactam products 8 and 9 depending on the substitution pattern of the enone moiety of the starting material. The structural identities and stereochemistry of the cyclized products have been determined by X-ray diffraction, and the diastereoselectivity in the formation of the 7-membered ring bislactam product was found to be 91.6% de. The mechanism of the cyclolactamization is discussed.
Databáze:	OpenAIRE
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