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The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
Laboratory of Organic Chemistry, Department of Chemistry, Aalto University, School of Science and Technology, PO Box 16100, Kemistintie 1, FI-00076 Aalto, Finland
* Author to whom correspondence should be addressed.
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 protecting group; enantiospecific; enantiopure
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MDPI and ACS Style
Karppanen, E.J.; Koskinen, A.M.P. The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis. Molecules 2010, 15, 6512-6547.
Karppanen EJ, Koskinen AMP. The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis. Molecules. 2010; 15(9):6512-6547.
Karppanen, Essi J.; Koskinen, Ari M. P. 2010. "The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis." Molecules 15, no. 9: 6512-6547.