Efficient Synthesis of Highly Enantioenriched Delta(1)-Pyrrolines

abstract

A general and efficient asymmetric synthesis of (1)-pyrrolines by a one-pot nitro-reduction, cyclization, and dehydration of (R,E)-1,5-diphenyl-3-(nitromethyl)-5-pent-4-en-1-ones with iron and aqueous hydrochloric acid has been developed. The (1)-pyrrolines were obtained with excellent enantioselectivities (up to 99%) and high yields (up to 83%).

keywords

ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; NITROMETHANE; PYRROLINES

subject category

Chemistry

authors

Resende, DISP; Guieu, S; Oliva, CG; Silva, AMS

our authors

acknowledgements

Thanks are due to the University of Aveiro and the Portuguese Fundacao para a Ciencia e a Tecnologia (FCT) for funding the Organic Chemistry Research Unit (project PEst- C/QUI/UI0062/2013), the CICECO Associate Laboratory (PEst-C/CTM/LA0011/2013) and the Portuguese National NMR Network (RNRMN). D.I.S.P.R. and S.G. also thank the FCT for a doctoral grant (SFRH/BD/62696/2009) and a postdoctoral grant (SFRH/BPD/70702/2010), respectively.

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