Straightforward Synthesis of α-Substituted Prolines by Cross-Metathesis

Autor:	Marco Lumini, Federica Pisaneschi, Franca M. Cordero, Alberto Brandi
Rok vydání:	2008
Předmět:	Chemistry Microwave heating Yield (chemistry) Organic Chemistry Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry Metathesis Selectivity Long chain Medicinal chemistry
Zdroj:	European Journal of Organic Chemistry. 2008:2817-2824
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200800044
Popis:	The synthesis of several α-substituted N-Boc-protected prolines has been achieved by cross metathesis (CM) of N-Boc-allylproline 5 with terminal long chain alkenes and alkenes bearing hydroxy, silyloxy, ester, and O-acetylglucosamido groups. The CM occurred with good selectivity and short reaction time under microwave heating conditions, affording yields in the range of 40–92 %. Addition of Ti(OiPr)4 as a Lewis acid allowed a slight increase of the yield in the case of alkenes with Lewis basic substituents. The CM was also successfully applied to allylproline protected with trichloroacetaldehyde 4, but the intermediate products were less practical for further deprotection and elaboration. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Databáze:	OpenAIRE
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