Organocatalytic Approach to (S)-1-Arylpropan-2-ols: Enantioselective Synthesis of the Key Intermediate of Antiepileptic Agent (−)-Talampanel

REFERENCES

• (a) Ariens , E. J. Stereochemistry: A source of problems in medicinal chemistry . Med. Res. Rev. 1986 , 6 , 451 ; (b) Federsel , H. J. Drug chirality-scaleup, manufacturing, and control . Chemtech. 1993 , 23 , 24 .
   PubMed Web of Science ®Google Scholar
• Anderson , B. A. ; Hansen , M. M. ; Harkness , A. R. ; Henry , C. L. ; Vicenzi , J. T. ; Zmijewski , M. J. Application of a practical biocatalytic reduction to an enantioselective synthesis of the 5H-2,3-benzodiazepine LY300164 . J. Am. Chem. Soc. 1995 , 117 , 12358 .
   Web of Science ®Google Scholar
• Acetti , D. ; Brenna , E. ; Fuganti , C. A new enzymatic approach to (R)-tamsulosin hydrochloride . Tetrahedron: Asymmetry 2007 , 18 , 488 .
   Google Scholar
• (a) Wagner , J. M. ; McElhinny , C. J. ; Lewin , A. H. ; Carroll , F. I. Stereospecific synthesis of amphetamines . Tetrahedron: Asymmetry 2003 , 14 , 2119 ; (b) Seggel , M. R. ; Yousif , M. Y. ; Lyon , R. A. ; Titeler , M. ; Roth , B. L. ; Suba , E. A. ; Glennon , R. A. A structure–affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors . J. Med. Chem. 1990 , 33 , 1032 ; (c) Tagliaro , F. ; Valentini , R. ; Manetto , G. ; Crivellente , F. ; Carli , G. ; Marigo , M. Hair analysis by using radioimmunoassay high performance liquid chromatography and capillary electrophoresis to investigate chronic exposure to heroin, cocaine, and/or ecstasy in applicants for driving licenses . Forensic Sci. Int. 2000 , 107 , 121 .
   Google Scholar
• (a) Kerti , G. ; Kurtan , T. ; Illyes , T.-Z. ; Kover , K. E. ; Solyom , S. ; Pescitelli , G. ; Fujioka , N. ; Berova , N. ; Antus , S. Enantioselective synthesis of 3-methylisochromans and determination of their absolute configurations by circular dichroism . Eur. J. Org. Chem. 2007 , 296 ; (b) Uchida , K. ; Fukuda , T. ; Iwao , M. Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline . Tetrahedron 2007 , 63 , 7178 .
   Web of Science ®Google Scholar
• (a) Brimble , M. A. ; Nairn , M. R. ; Prabaharan , H. Synthetic strategies towards pyranonaphthoquinone antibiotics . Tetrahedron 2000 , 56 , 1937 ; (b) Donner , C. D. ; Gill , M. Pigments of fungi, part 68: Synthesis and absolute configuration of thysanone . J. Chem. Soc., Perkin Trans. 1 2002 , 938 .
   Web of Science ®Google Scholar
• Sawant , R. T. ; Waghmode , S. B. Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone . Tetrahedron 2009 , 65 , 1599 .
   Web of Science ®Google Scholar
• (a) Easwar , S. ; Argade , N. P. Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol: An efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (−)-talampanel. Tetrahedron: Asymmetry 2003, 14, 333; (b) Kiss , V. ; Egri , G. ; Balint , J. ; Ling , I. ; Barkoczi , J. ; Fogassy , E. Kinetic and chemical resolution of different 1-phenyl-2-propanol derivatives. Tetrahedron: Asymmetry 2007, 17, 2220.
   Google Scholar
• (a) Noyori , R. ; Tomino , I. ; Tanimoto , Y. ; Nishizawa , M. Rational designing of efficient chiral reducing agents: Highly enantioselective of aromatic ketones by binaphthol-modified lithium aluminum hydride reagents reduction . J. Am. Chem. Soc. 1984 , 106 , 6709 ; (b) Kim , Y. H. ; Park , D. H. ; Byun , I. S. ; Yoon , I. K. ; Park , C. S. Stereocontrolled catalytic asymmetric reduction of ketones with oxazaborolidines derived from new chiral amino alcohols . J. Org. Chem. 1993 , 58 , 4511 ; (c) Yamamoto , K. ; Ueno , K. ; Naemura , K. Asymmetric hydride reduction using a chiral aluminium reagent modified by a crowned 2,2′-dihydroxy-1,1′-binaphthyl . J. Chem. Soc., Perkin Trans. 1 1991 , 2607 .
   Web of Science ®Google Scholar
• (a) Inoue , K. ; Makino , Y. ; Itoh , N. Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH) . Tetrahedron Asymmetry 2005 , 16 , 2539 ; (b) Erdelyi , B. ; Szabo , A. ; Seres , G. ; Birincsik , L. ; Ivanics , J. ; Szatzkerd , G. ; Popped , L. Stereoselective production of (S)-1-araalkyl- and 1-arylethanols by freshly harvested and lyophilized yeast cells . Tetrahedron: Asymmetry 2006 , 17 , 268 .
   Google Scholar
• Talluri , S. K. ; Sudalai , A. An organo-catalytic approach to the enantioselective synthesis of (R)-selegiline . Tetrahedron 2007 , 63 , 9758 .
   Web of Science ®Google Scholar
• (a) Dalko , P. I. ; Moisan , L. In the golden age of organocatalysis . Angew. Chem. Int. Ed. 2004 , 43 , 5138 ; (b) Houk , K. N. ; List , B. Asymmetric organocatalysis . Acc. Chem. Res. 2004 , 37 , 487 ; (c) List , B. ; Seayad , J. Asymmetric organocatalysis . Org. Biomol. Chem. 2005 , 3 , 719 .
   PubMed Web of Science ®Google Scholar
• (a) Movassaghi , M. ; Jacobsen , E. N. The simplest “enzyme.” Science 2002 , 298 , 1904 ; (b) List , B. Proline-catalyzed asymmetric reactions . Tetrahedron 2002 , 58 , 5573 ; (c) List , B. The simplest “enzyme” enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents . Acc. Chem. Res. 2004 , 37 , 548 ; (d) Dalko , P. I. ; Moisan , L. Enantioselective organocatalysis . Angew. Chem. Int. Ed. 2001 , 40 , 3726 .
   PubMed Web of Science ®Google Scholar
• (a) Hayashi , Y. ; Yamaguchi , J. ; Hibino , K. ; Shoji , M. Direct proline-catalyzed asymmetric α-aminooxylation of aldehydes . Tetrahedron Lett. 2003 , 44 , 8293 ; (b) Zhong , G. A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric α-aminoxylation of aldehydes . Angew. Chem. Int. Ed. 2003 , 42 , 4247 ; (c) Brown , S. P. ; Brochu , M. P. ; Sinz , C. J. ; MacMillan , D. W. C. The direct and enantioselective organocatalytic α-oxidation of aldehydes . J. Am. Chem. Soc. 2003 , 125 , 10808 ; (d) Hayashi , Y. ; Yamaguchi , J. ; Sumiya , T. ; Hibino , K. ; Shoji , M. Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones . J. Org. Chem. 2004 , 69 , 5966 .
   Web of Science ®Google Scholar
• (a) For 2a, see Leopold , D. ; Fischer , H. EPR studies on the photofragmentation of 2,2-dialkyl-2-alkylaminoacetophenones . J. Chem. Soc., Perkin Trans. 2 1992 , 513 ; (b) for 2b, see Denniff , P. ; Whiting , D. A. Synthesis of (±)-[6]-gingerol (pungent principle of ginger) and relatives via directed aldol reactions . J. Chem. Soc., Chem. Commun. 1976 , 712 ; (c) for 2c, see Schobert , R. ; Siegfried , S. ; Gordon , G. J. Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family . J. Chem. Soc., Perkin Trans. 1 2001 , 2393 ; (d) for 2d, see Frost , C. G. ; Hartley , B. C. Tandem molybdenum-catalyzed hydrosilylations: An expedient synthesis of β-aryl aldehydes . Org. Lett. 2007 , 9 , 4259 ; (e) for 2e see, Ref. 7 .
   Google Scholar
• Martinelli , M. J. ; Vaidyanathan , R. ; Pawlak , J. M. ; Nayyar , N. K. ; Dhokte , U. P. ; Doecke , C. W. ; Zollars , L. M. H. ; Moher , E. D. ; Khau , V. V. ; Kosmrlj , B. Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight . J. Am. Chem. Soc. 2002 , 124 , 3758 .
   Web of Science ®Google Scholar
• (a) For 3a , Narina , S. V. ; Talluri , S. K. ; George , S. ; Sudalai , A. Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation. Tetrahedron Lett. 2007, 48, 65; (b) for 3b, see Hiroe , K. ; Sanae , H. ; Yayoi , K. ; Nobuji , N. Antioxidative phenylpropanoids from berries of Pimenta dioica . Phytochemistry 1999, 52, 1307; Kelley , C. J. ; Mahajan , J. R. ; Brooks , L. C. ; Neubert , L. A. ; Breneman , W. R. ; Carmack , M. Polyphenolic acids of Lithospermum ruderale (Boraginaceae), I: Isolation and structure determination of lithospermic acid. J. Org. Chem. 1975, 40, 1804; (c) for 3c , Rama , M. H. ; Rao , A. S. Enantioselective synthesis of (R)-(+)-safrole oxide. Indian J. Chem. 1998, 37B, 78; (d) for 3e, see Ref. 7.
   Web of Science ®Google Scholar
• (a) For 1a, see Ref. 3; Donzelli , F. ; Fuganti , C. ; Mendozza , M. ; Pedrocchi-Fantoni , G. ; Servi , S. ; Zucchi , G. On the stereochemistry of the Baeyer–Villiger degradation of arylalkylketones structurally related to raspberry ketone by Beauveria bassiana . Tetrahedron Asymmetry 1996 , 7 , 3129 ; (b) for 1b, see Ref. 5a; (c) for 1c, see Ref. 8a; (d) for 1d, see Ref. 4a; (e) for 1e, see Ref. 7 .
   Google Scholar