Next Article in Journal
New 2-Arylbenzofurans from the Root Bark of Artocarpus lakoocha
Next Article in Special Issue
Protecting Groups in Carbohydrate Chemistry: Influence on Stereoselectivity of Glycosylations
Previous Article in Journal
Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
Previous Article in Special Issue
Synthesis and Application of a 2-[(4-Fluorophenyl)-sulfonyl]ethoxy Carbonyl(Fsec) Protected Glycosyl Donor in Carbohydrate Chemistry
Article Menu

Article Versions

Export Article

Open AccessReview
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)
Download PDF [1102 KB, uploaded 18 June 2014]   |  

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 phenylfluorenyl; amino acid; nitrogen protecting group; enantiospecific; enantiopure
Figures

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

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top