Issue 34, 2012
From the journal:

Organic & Biomolecular Chemistry

Double diastereoselection in anti aldol reactions mediated by dicyclohexylchloroborane between an l-erythrulose derivative and chiral aldehydes†‡

Santiago Díaz-Oltra,a   Purificación Ruiz,a   Eva Falomir,a   Juan Murga,a   Miguel Carda*a  and  J. Alberto Marco*b  

* Corresponding authors

a Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, E-12071 Castellón, Spain
E-mail: mcarda@qio.uji.es
Fax: +34-964-728214
Tel: +34 -964-728242

b Depart. de Q. Orgánica, Univ. de Valencia, E-46100 Burjassot, Valencia, Spain
E-mail: alberto.marco@uv.es
Fax: +34-96-3544328
Tel: +34 -96-3544337

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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Article information

DOI
https://doi.org/10.1039/C2OB25803J
Article type
Paper
Submitted
26 Apr 2012
Accepted
21 Jun 2012
First published
24 Jul 2012

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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