Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines

Abstract Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel–Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA–Asp(OBn)–OMe and Friedel–Crafts acylation of phenol with N-TFA–Asp(Cl)–OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

[1]  T. Hemscheidt,et al.  Homotyrosine-containing cyanopeptolins 880 and 960 and anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8. , 2009, Journal of natural products.

[2]  M. Hashimoto,et al.  Effective Synthesis of Optically Active Trifluoromethyldiazirinyl Homophenylalanine and Aroylalanine Derivatives with the Friedel-Crafts Reaction in Triflic Acid , 2009, Bioscience, biotechnology, and biochemistry.

[3]  F. Weygand,et al.  N‐Trifluoracetyl‐aminosäuren, X. N‐Trifluoracetyl‐L‐Asparaginsäure‐Anhydrid und N‐Trifluoracetyl‐L‐Prolin‐Anhydrid , 1957 .

[4]  R. Weiss,et al.  Photorearrangements of Five 1- and 2-Naphthyl Acylates in Three Unstretched and Stretched Polyethylene Films. Does Reaction Selectivity Correlate with Free Volumes Measured by Positron Annihilation Lifetime Spectroscopy? , 2000 .

[5]  N. Roques,et al.  Metal triflates–methanesulfonic acid as new catalytic systems: application to the Fries rearrangement , 2003 .

[6]  J. Kilburn,et al.  Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids , 2005 .

[7]  I. Hachiya,et al.  Hafnium trifluoromethanesulfonate (Hf(OTf)4) as an efficient catalyst in the fries rearrangement and direct acylation of phenol and naphthol derivatives , 1996 .

[8]  M. Sugiura,et al.  Rare-earth metal triflates in organic synthesis. , 2002, Chemical reviews.

[9]  F. Effenberger,et al.  Catalytic Friedel-Crafts Acylation of Aromatic Compounds† , 1972 .

[10]  F. Effenberger,et al.  Trifluoromethanesulfonic-Carboxylic Anhydrides, Highly Active Acylating Agents") , 1972 .

[11]  Luis Castedo,et al.  Synthesis of ω-(Hetero)arylalkynylated α-Amino Acid by Sonogashira-Type Reactions in Aqueous Media , 2006 .

[12]  J. Hasegawa,et al.  A highly efficient asymmetric synthesis of methoxyhomophenylalanine using michael addition of phenethylamine , 1998 .

[13]  S. Kang,et al.  Facile synthesis and photo-Fries rearrangement of 2-benzoyl-4-benzoyloxyphenol leading to dibenzoyldihydroxybenzene derivatives , 2003 .

[14]  B. Kaboudin.  Methanesulfonic acid/phosphorus oxychloride (MAPO) as a new efficient reagent in the Fries rearrangement , 1999 .

[15]  Raphael Dumeunier,et al.  On the role of triflic acid in the metal triflate-catalysed acylation of alcohols , 2004 .

[16]  Ze-Zhen He,et al.  Amino Acid Anhydride Hydrochlorides as Acylating Agents in Friedel-Crafts Reaction: A Practical Synthesis of l-Homophenylalanine , 2001 .

[17]  F. Effenberger,et al.  The First Unequivocal Evidence of the Reacting Electrophile in Aromatic Acylation Reactions1 , 1996 .

[18]  M. Ciufolini,et al.  Fully stereocontrolled total syntheses of (-)-cylindricine C and (-)-2-epicylindricine C: a departure in sulfonamide chemistry. , 2004, Angewandte Chemie.

[19]  K. Park,et al.  Facile synthesis of regio-isomeric naphthofurans and benzodifurans , 2005 .

[20]  A. Weissberger,et al.  The Introduction of n-Alkyl Groups into Phenols and Hydroquinones , 1960 .

[21]  D. Melillo,et al.  Practical enantioselective synthesis of a homotyrosine derivative and (R,R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist , 1987 .

[22]  Zhi Li,et al.  DPAMPP in catalytic asymmetric reactions: enantioselective synthesis of l-homophenylalanine , 2000 .

[23]  M. Hashimoto,et al.  EFFECTIVE SYNTHESIS OF OPTICALLY ACTIVE 3-PHENYL-3-(3-TRIFLUOROMETHYL) DIAZIRINYL BISHOMOPHENYLALANINE DERIVATIVES , 2009 .

[24]  Tongxing Wu,et al.  The synthesis of l-(+)-homophenylalanine hydrochloride , 2000 .

[25]  Jianhua Wang,et al.  Preparative isolation and purification of acetophenones from the Chinese medicinal plant Cynanchum bungei Decne. by high-speed counter-current chromatography , 2008 .

[26]  George A. Olah,et al.  Friedel-Crafts and related reactions , 1963 .

[27]  C. Bewley,et al.  Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp. , 2006, The Journal of organic chemistry.

[28]  W. Wolf,et al.  Trifluoromethanesulfonic acid mediated Friedel–Crafts reaction of (E)-3-aryl-2-(diethoxyphosphoryl)acrylic acids with electron-rich hydroxyarenes. A convenient approach to α-methylene-δ-valerolactones , 2007 .

[29]  R. Roberts,et al.  Studies in trifluoromethanesulphonic acid—IV , 1983 .

[30]  R. Haszeldine,et al.  Alkyltrifluoromethanesulphonates as alkylating reagents for aromatic compounds , 1980 .

[31]  P. Cole,et al.  Protein tyrosine kinase Csk-catalyzed phosphorylation of Src containing unnatural tyrosine analogues. , 2001, Journal of the American Chemical Society.

[32]  M. Hashimoto,et al.  Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-Crafts reaction with trifluoromethanesulfonic acid , 2008 .

[33]  K. Sugamoto,et al.  The Friedel–Crafts acylation of aromatic compounds with carboxylic acids by the combined use of perfluoroalkanoic anhydride and bismuth or scandium triflate , 2004 .

[34]  A. Griesbeck,et al.  A Simple Approach to β-Amino Acids by Acylation of Arenes with N-Acyl Aspartic Anhydrides , 1997 .

[35]  F. G. Njoroge,et al.  A short enantiospecific synthesis of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) , 1985 .

[36]  M. Micklus,et al.  Stereochemistry of friedel-crafts addition of phthalylaspartic anhydride to benzene , 1976 .

[37]  Robert J. Martin.  USES OF THE FRIES REARRANGEMENT FOR THE PREPARATION OF HYDROXYARYLKETONES. A REVIEW , 1992 .