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DOI: 10.1055/s-0033-1339291
Stereoselective Synthesis of Chiral Pyrrolidine Derivatives of (+)-α-Pinene Containing a β-Amino Acid Moiety
Publikationsverlauf
Received: 30. April 2013
Accepted after revision: 27. Mai 2013
Publikationsdatum:
09. August 2013 (online)
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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 - peptidesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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