The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis

Essi J. Karppanen, Ari M.P. Koskinen

    Research output: Contribution to journalArticleScientificpeer-review

    10 Citations (Scopus)
    136 Downloads (Pure)

    Abstract

    One of the biggest challenges in asymmetric synthesis is to prevent racemization
    of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis.
    Original languageEnglish
    Pages (from-to)6512-6547
    JournalMOLECULES
    Volume15
    Issue number9
    DOIs
    Publication statusPublished - 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

    • 9-Phenyl-9-fluorenyl
    • phenylfluorenyl
    • amino acid
    • nitrogen protecting group
    • enantiospecific
    • enantiopure

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