Stereoselective Synthesis of Chiral Pyrrolidine Derivatives of (+)-α-Pinene Containing a β-Amino Acid Moiety

Alberto Vega-Peñaloza; Omar Sánchez-Antonio; Margarita Escudero-Casao; Gábor Tasnádi; Ferenc Fülöp; Eusebio Juaristi

doi:10.1055/s-0033-1339291

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(17): 2458-2468
DOI: 10.1055/s-0033-1339291

paper

Stereoselective Synthesis of Chiral Pyrrolidine Derivatives of (+)-α-Pinene Containing a β-Amino Acid Moiety

Alberto Vega-Peñaloza

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México D.F., México Fax: +52(55)57473897 eMail: juaristi@relaq.mx

,

Omar Sánchez-Antonio

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México D.F., México Fax: +52(55)57473897 eMail: juaristi@relaq.mx

,

Margarita Escudero-Casao

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México D.F., México Fax: +52(55)57473897 eMail: juaristi@relaq.mx

,

Gábor Tasnádi

^bInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

,

Ferenc Fülöp

^bInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary

,

Eusebio Juaristi*

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México D.F., México Fax: +52(55)57473897 eMail: juaristi@relaq.mx

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Abstract

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Abstract

We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported.

Key words

stereoselective synthesis - chiral pool - enantiopure β-amino acids - coupling reactions - peptides

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Referenzen

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