scholarly journals Sterically Controlled Syntheses of Optically Active Organic Compounds. XX. Synthesis of Optically Active Alanine from α-Bromopropionamides

1973 ◽  
Vol 46 (6) ◽  
pp. 1869-1872 ◽  
Author(s):  
Tadashi Okawara ◽  
Kaoru Harada
Keyword(s):  
Organic Compounds ◽  
Optically Active

Controlled racemization of optically active organic compounds: Prospects for asymmetric transformation

Tetrahedron ◽  
1997 ◽  
Vol 53 (28) ◽  
pp. 9417-9476 ◽  
Author(s):  
Eelco J. Ebbers ◽  
Gerry J.A. Ariaans ◽  
Joannes P.M. Houbiers ◽  
Alle Bruggink ◽  
Binne Zwanenburg
Keyword(s):  
Organic Compounds ◽  
Optically Active ◽  
Asymmetric Transformation

scholarly journals Development of N-F fluorinating agents and their fluorinations: Historical perspective

2021 ◽  
Vol 17 ◽  
pp. 1752-1813
Author(s):  
Teruo Umemoto ◽  
Yuhao Yang ◽  
Gerald B Hammond
Keyword(s):  
Organic Compounds ◽  
Historical Development ◽  
Historical Perspective ◽  
Optically Active ◽  
Research Areas ◽  
Troger's Base

This review deals with the historical development of all N-F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. N-F agents have proven useful by virtue of their easy handling. This reagent class includes many types of N-F compounds: perfluoro-N-fluoropiperidine, N-fluoro-2-pyridone, N-fluoro-N-alkylarenesulfonamides, N-fluoropyridinium salts and derivatives, N-fluoroquinuclidium salts, N-fluoro-trifluoromethanesulfonimide, N-fluoro-sultams, N-fluoro-benzothiazole dioxides, N-fluoro-lactams, N-fluoro-o-benzenedisulfonimide, N-fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluorodinitroimidazole, N-fluoro-trichloro-1,3,5-triazinium salt, N-F ethano-Tröger’s base derivatives, N-fluoro-methanesulfonimide, N-fluoro-N-arylarenesulfonamides, bisN-F salts such as N,N’-difluorobipyridinium salts and N,N’-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral N-F reagents such as optically active N-fluoro-sultam derivatives, N-fluoro-alkaloid derivatives, DABCO-based N-F derivatives, and N-F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective.

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