Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

• Holger Erdbrink,
• Elisabeth K. Nyakatura,
• Susanne Huhmann,
• Ulla I. M. Gerling,
• Dieter Lentz,
• Beate Koksch and
• Constantin Czekelius

Beilstein J. Org. Chem. 2013, 9, 2009–2014, doi:10.3762/bjoc.9.236

• propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4’-F3Ile. Keywords: amino acids; CD-spectroscopy; fluorine; helix propensity; organo-fluorine; trifluoroisoleucine; Introduction Due to the unique physicochemical properties of fluorine, namely its small size

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

• Assaad Nasr El Dine,
• Ali Khalaf,
• Danielle Grée,
• Olivier Tasseau,
• Fares Fares,
• Nada Jaber,
• Philippe Lesot,
• Ali Hachem and
• René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

• successfully developed for these sequential reactions. By carrying out various types of Pd-catalyzed coupling reactions for compounds with a p-bromophenyl substituent a route to focused chemical libraries was demonstrated. Keywords: 19F/1H HOESY; gem-difluoroalkyl derivatives; organo-fluorine compounds

The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes

• Yi Wang,
• Peer Kirsch,
• Tomas Lebl,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2012, 8, 1271–1278, doi:10.3762/bjoc.8.143

• –F bond endo into the ring, and appear to benefit from C–CHF–C angle widening, which relaxes 1,4-H,H transannular interactions. Keywords: alicyclic chemistry; conformational analysis; cyclododecane; 19F NMR; organo-fluorine chemistry; transannular interactions; Introduction The conformation of

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

• Guillaume G. Launay,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 41, doi:10.3762/bjoc.6.41

• . Keywords: 4-fluoropiperidine; 4-fluoropyran; heterocycles; organo-fluorine chemistry; Prins cyclisation; Introduction Selective incorporation of the C–F bond into organic molecules can impart useful and attractive properties to performance materials [1][2][3]. To this end there are a useful but relatively

Organo-fluorine chemistry II

• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 36, doi:10.3762/bjoc.6.36

• David O'Hagan School of Chemistry, University of St Andrews, Fife, KY16 9ST, United Kingdom 10.3762/bjoc.6.36 It is a pleasure to be able to introduce this second Thematic Series on ‘organo-fluorine chemistry’ within the Beilstein Journal of Organic Chemistry. The series now embeds the subject

• firmly as a special interest area of the journal. The first series in 2008 presented contributions representing a wide range of organic fluorine chemistry [1][2][3][4][5][6][7][8][9][10] and this series continues that trend exploring the synthesis and properties of a new range of organo-fluorine

• industry servicing these industrial sectors. New innovations and insights into the synthesis and the nature and behaviour of organo-fluorine compounds continue to intrigue and this Thematic Series offers a glimpse into the level of activity in the area. I am delighted that all of the authors have agreed to

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

• Vincent A. Brunet,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2009, 5, No. 61, doi:10.3762/bjoc.5.61

• diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy. Keywords: C–F bond; organo–fluorine chemistry; stereospecific fluorination; vicinal trifluoro motif; Introduction Selective fluorination is an important strategy for the design of performance molecules

Themed series in organo- fluorine chemistry

• David O'Hagan

Beilstein J. Org. Chem. 2008, 4, No. 11, doi:10.3762/bjoc.4.11

• David O'Hagan School of Chemistry, University of St Andrews, Fife, KY16 9ST 10.3762/bjoc.4.11 It is a great pleasure to be able to introduce this Themed series on organo-fluorine chemistry in the Beilstein Journal of Organic Chemistry. The introduction of fluorine into organic molecules is widely

• ]. Organo-fluorine compounds have also found a significant role in soft materials chemistry such as liquid crystals, photoresist polymers and self assembling monolayers [3]. Allied to this breadth of activity is a steady development in the number and range of fluorination reagents and methodologies. DAST

• enabling elemental fluorine to be used in large scale organo-fluorine production [4]. The introduction in the early 1990's of air stable electrophilic fluorinating reagents such as Selectfluor [5] has been revolutionary and has opened up many new methods for fluorine introduction, and provided the

Stereoselective α-fluoroamide and α-fluoro- γ-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement

• Kenny Tenza,
• Julian S. Northen,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2005, 1, No. 13, doi:10.1186/1860-5397-1-13

• fluorine at the stereogenic centre. Introduction The development of methods for the stereoselective introduction of the C-F bond, α-to a carbonyl group has been a significant and recent focus in organo-fluorine chemistry.[1][2] Most effort has involved enolate reactions with electrophilic fluorinating