Issue 7, 2011
From the journal:

Organic & Biomolecular Chemistry

Highly stereoselective double (R)-phenylglycinol-induced cyclocondensation reactions of symmetric aryl bis(oxoacids)†‡

Mercedes Amat,*a   Carlos Arróniz,a   Elies Molins,b   Carmen Escolano*a  and  Joan Boscha  

* Corresponding authors

a Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), 08028-Barcelona, Spain
E-mail: amat@ub.edu, cescolano@ub.edu

b Institut de Ciència de Materials de Barcelona (CSIC), Campus UAB, 08193-Cerdanyola, Spain
E-mail: elies@icmab.es

Abstract

The double cyclocondensation of symmetric pyridyl bis(oxoacids) 2b and 3b with (R)-phenylglycinol stereoselectively gave access to bis-phenylglycinol-derived oxazolopyrrolidine 9 and oxazolopiperidone 10, respectively. Application of the stereocontrolled cyclocondensation reaction to phenyl bis-γ-oxoacid 4b provided 11, which was converted to the corresponding enantiopure di(pyrrolidinyl)benzene 22. The absolute configuration of the new stereogenic centers generated in the key cyclocondenstion step was unambiguously established by X-ray crystallographic analysis.

Graphical abstract: Highly stereoselective double (R)-phenylglycinol-induced cyclocondensation reactions of symmetric aryl bis(oxoacids)

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Article information

DOI
https://doi.org/10.1039/C0OB00970A
Article type
Paper
Submitted
02 Nov 2010
Accepted
22 Dec 2010
First published
23 Dec 2010

Org. Biomol. Chem., 2011,9, 2175-2184

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Highly stereoselective double (R)-phenylglycinol-induced cyclocondensation reactions of symmetric aryl bis(oxoacids)

M. Amat, C. Arróniz, E. Molins, C. Escolano and J. Bosch, Org. Biomol. Chem., 2011, 9, 2175 DOI: 10.1039/C0OB00970A

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