The effectiveness of proteinogenic amino acids in the asymmetric aldol reaction in DMSO and aqueous DMSO

Yujiro Hayashi, Takahiko Itoh, Norio Nagae, Masahiro Ohkubo, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

The effects of twenty proteinogenic amino acids have been investigated in the aldol reaction of aldehyde and ketone in DMSO and aqueous DMSO (in the presence of three equivalents of water). Not only proline but also other amino acids promote the al-dol reaction enantioselectively. The effect of water varies with amino acid, and water does not affect the enantioselectivity in most cases, the exceptions being Pro, Ser and His. In the case of Pro, large positive effects on diastereo- and enantioselectivities were ob-served in the reaction of a-substituted methyl ketone, while no ef-fect was observed in that of methyl ketone.

Original languageEnglish
Pages (from-to)1565-1570
Number of pages6
JournalSynlett
Issue number10
DOIs
Publication statusPublished - 2008 Jun 13

Keywords

  • asymmetric synthesis, aldol reactions, organocatalyst, amino acids, water

ASJC Scopus subject areas

  • Organic Chemistry

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