Synthesis 2017; 49(02): 299-309
DOI: 10.1055/s-0036-1588620
paper
© Georg Thieme Verlag Stuttgart · New York

Multicomponent Diastereoselective Synthesis of Indolizidines via 1,3-Dipolar Cycloadditions of Azomethine Ylides

Luis M. Castelló
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080-Alicante, Spain
b  Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, 03080-Alicante, Spain   Email: cnajera@ua.es
c   Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain
,
Verónica Selva
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080-Alicante, Spain
b  Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, 03080-Alicante, Spain   Email: cnajera@ua.es
c   Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain
,
Carmen Nájera*
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080-Alicante, Spain
c   Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain
,
José M. Sansano
a  Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080-Alicante, Spain
b  Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, 03080-Alicante, Spain   Email: cnajera@ua.es
c   Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain
› Author Affiliations
Further Information

Publication History

Received: 31 July 2016

Accepted after revision: 10 September 2016

Publication Date:
19 October 2016 (eFirst)

Dedicated to Professor Dieter Enders.

Abstract

The synthesis of polyfunctionalized indolizidines from pipecolinic acid alkyl ester derivatives, aldehydes and a wide range of dipolarophiles by multicomponent 1,3-dipolar cycloadditions is developed in a diastereoselective manner. The cycloadditions take place in toluene with short reaction times at 70 °C, giving good yields. The synthesis of these fused heterocycles is also studied starting from pipecolinic acid, generating the dipole through a decarboxylative route at 120 °C. The relative configuration of the resulting products as well as the mechanistic pathways are also explained.

Supporting Information

 
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