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Molecules 2010, 15(9), 6512-6547; doi:10.3390/molecules15096512

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 / Revised: 13 September 2010 / Accepted: 14 September 2010 / Published: 17 September 2010
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
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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 phenylfluorenyl; amino acid; nitrogen protecting group; enantiospecific; enantiopure

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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