Diastereoselective direct aldol reaction and subsequent cyclization of 2-azetidinone-tethered azides for the preparation of a 4-hydroxypipecolic acid analogue

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ECSOC-13 | General Organic Synthesis

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13th Int. Electron. Conf. Synth. Org. Chem. 2009, a015:1-6

Communication

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Diastereoselective direct aldol reaction and subsequent cyclization of 2-azetidinone-tethered azides for the preparation of a 4-hydroxypipecolic acid analogue

Benito Alcaide ^a

, Pedro Almendros ^b

and Amparo Luna ^a^,*

a Departamento de Química Orgánica I. Facultad de Química. Universidad Complutense de Madrid, 28040-Madrid, Spain; b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain; * Author to whom correspondence should be addressed.

(This article belongs to the section A. General Organic Synthesis)

Cite this paper as: Alcaide, B.; Almendros, P.; Luna, A. Diastereoselective direct aldol reaction and subsequent cyclization of 2-azetidinone-tethered azides for the preparation of a 4-hydroxypipecolic acid analogue. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, a015:1-6.

Abstract: The reaction of enantiopure 3-azido-4-oxoazetidine-2-carbaldehyde with acetone was catalyzed by L-proline, to give the corresponding aldol adduct. This product was stereocontrolled cyclized by using intramolecular reductive amination achieving a new 4-hydroxypipecolic acid analogue with a bicyclic b-lactam structure.

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