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Issue 34, 2012
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Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an L-erythrulose derivative and chiral aldehydes

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Abstract

Anti aldol reactions of an L-erythrulose derivative with several α-chiral aldehydes mediated by dicyclohexylboron chloride are examined. Good yields and stereoselectivities are observed. The results are best explained when the reactions are assumed to occur via boat-like transition states with minimization of 1,3-allylic strain and avoidance of syn pentane interactions.

Graphical abstract: Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an l-erythrulose derivative and chiral aldehydes

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Publication details

The article was received on 26 Apr 2012, accepted on 21 Jun 2012 and first published on 24 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB25803J
Citation: Org. Biomol. Chem., 2012,10, 6937-6944
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    Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an L-erythrulose derivative and chiral aldehydes

    S. Díaz-Oltra, P. Ruiz, E. Falomir, J. Murga, M. Carda and J. A. Marco, Org. Biomol. Chem., 2012, 10, 6937
    DOI: 10.1039/C2OB25803J

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