the 9-phenyl-9-fluorenyl group for nitrogen protection in enantiospecific synthesis9-phenyl-9-fluorenyl组enantiospecific合成的氮保护.pdfVIP

Molecules 2010, 15, 6512-6547; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis Essi J. Karppanen and Ari M. P. Koskinen * Laboratory of Organic Chemistry, Department of Chemistry, Aalto University, School of Science and Technology, PO Box 16100, Kemistintie 1, FI-00076 Aalto, Finland; E-Mail: essi.karppanen@tkk.fi * Author to whom correspondence should be addressed; E-Mail: ari.koskinen@tkk.fi; Tel.: +358-9-470 22526; Fax: +358-9-470 22538. Received: 12 August 2010; in revised form: 13 September 2010 / Accepted: 14 September 2010 / Published: 17 September 2010 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. Keywords: phenylfluorenyl; amino acid; nitrogen