Stereoselectivity in formation of oxacephams from 1,3-alkylidene-threitols

Autor:	Patrycja Szczukiewicz, Marek Chmielewski, Beata Przykorska, Jadwiga Frelek, Katarzyna Borsuk, Barbara Grzeszczyk
Rok vydání:	2004
Předmět:	Pharmacology Alternative methods Carbon atom Stereochemistry Organic Chemistry Enantioselective synthesis Absolute configuration Erythritol Catalysis Cycloaddition Analytical Chemistry chemistry.chemical_compound Stereospecificity chemistry Drug Discovery Stereoselectivity Spectroscopy
Zdroj:	Chirality. 16:414-421
ISSN:	1520-636X 0899-0042
DOI:	10.1002/chir.20058
Popis:	The [2+2]cycloaddition of CSI to the (Z)-propenyl ethers derived from respective 1,3-methylidene- and 1,3-ethylidene-threitols, contrary to the corresponding erythritol derivatives, is characterized by a low stereoselectivity and a lack of stereospecificity. On the other hand, the alternative method of the oxacepham formation, based on the 4-vinyloxy-azetidinone, proceeds with an excellent stereoselectivity. The CD-spectroscopy offers an attractive tool for determination of the absolute configuration of the bridgehead carbon atom at the 5-oxacepham skeleton.
Databáze:	OpenAIRE
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