Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction

Autor:	Sebastian Stecko, Bartłomiej Furman, Kamil Kabala, Marek Chmielewski, Barbara Grzeszczyk
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Substituent chemistry.chemical_element Alkyne Ring (chemistry) Combinatorial chemistry Nitrone chemistry.chemical_compound chemistry Lithium borohydride Lithium Monobactams Glyoxylic acid
Zdroj:	The Journal of Organic Chemistry. 80:12038-12046
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.5b01979
Popis:	A Kinugasa reaction between copper(I) acetylides and cyclic nitrones derived from chiral amino alcohols and glyoxylic acid is reported. The stereochemical preferences observed in this reaction are discussed. The alkyne molecule approaches the nitrone exclusively anti to the large substituent next to the nitrogen atom to provide the cis-substituted β-lactam ring preferentially. The six-membered oxazinone ring can be opened by reduction with lithium borohydride. Deprotection of the β-lactam nitrogen atom can be achieved by lithium in liquid ammonia reduction or by CAN oxidation, depending on the substituents attached to the four-membered azetidinone ring. The adducts obtained by the Kinugasa reaction provide an attractive entry to a variety of monocyclic β-lactam structures related to monobactams and nocardicins.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f8d2ae06f98dd85bc2d6d0a4b66b94d7 https://doi.org/10.1021/acs.joc.5b01979 Zobrazit plný text záznamu