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Synthesis 2005(14): 2345-2348
DOI: 10.1055/s-2005-870021
DOI: 10.1055/s-2005-870021
PAPER
© Georg Thieme Verlag Stuttgart · New York
Hydrolytic Kinetic Resolution of α-Naphthyl Glycidyl Ether: A Practical Access to Highly Enantioselective β-Adrenergic Blocking Agents
Further Information
Received
15 February 2005
Publication Date:
13 July 2005 (online)
Publication History
Publication Date:
13 July 2005 (online)
Abstract
Kinetic resolution of (±)-naphthyl glycidyl ether using 0.5 mol% (R,R)-salen Co(III)OAc and water (0.55 equiv) provided enantiomerically pure naphthyl glycidyl ether and 1-naphthylglycerol derivatives with high enantiomeric excess. Application of this approach to highly enantioenriched (S)-naftopidil and (S)-propranolol is described.
Key words
naphthyl glycidyl ether - hydrolytic kinetic resolution - naftopidil - propranolol - terminal epoxide
- 1
Crosby J. Tetrahedron 1991, 47: 4789 - 2
Decamp WH. Chirality 1989, 1: 2 - For leading reviews, see:
-
3a
Johnson RA.Sharpless KB. Catalytic Asymmetric Epoxidation of Allylic Alcohols, In Catalytic Asymmetric SynthesisOjima I. VCH; New York: 1993. p.103-158 -
3b
Katsuki T.Martin VS. Org. React. 1996, 48: 1 - For leading reviews, see:
-
4a
Jacobsen EN.Wu MH. In Comprehensive Asymmetric CatalysisJacobsen EN.Pfaltz A.Yamamoto H. Springer; New York: 1999. Chap. 182. -
4b
Jacobsen EN. . Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins, In Catalytic Asymmetric SynthesisOjima I. VCH; New York: 1993. p.159 -
4c
Collman JP.Zhang X.Lee VJ.Uffelman ES.Brauman JI. Science (Washington, DC, U. S.) 1993, 261: 1404 -
4d
Katsuki T. Asymmetric Epoxidation of Unfunctionalized Olefins and Related Reactions, In Catalytic Asymmetric SynthesisOjima I. VCH; New York: 2000. p.287 - For recent reviews, see:
-
5a
Porter MJ.Skidmore J. Chem. Commun. 2000, 1215 -
5b
Nemoto T.Ohshima T.Shibasaki M. J. Synth. Org. Chem. Jpn. 2002, 60: 94 -
6a
Tokunaga M.Larrow JF.Kakiuchi F.Jacobsen EN. Science 1997, 277: 936 -
6b
Schaus SE.Brandes BD.Larrow JF.Tokunaga M.Hansen KB.Gould AE.Furrow ME.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 1307 -
6c
Larrow JF.Hemberger KE.Jasmin S.Kabir H.Morel P. Tetrahedron: Asymmetry 2003, 14: 3589 -
6d
Song Y.Yao X.Chen H.Bai C.Hu X.Zheng Z. Tetrahedron Lett. 2002, 43: 6625 -
6e
Bose DS.Narsaiah AV. Bioorg. Med. Chem. 2005, 13: 627 - 7 Drugs Future 2000, 25: 93
- For recently reported preparations of (S)-propranolol by non-enzymatic asymmetric synthesis, see:
-
8a
Sasai H.Itoh N.Suzuki T.Shibasaki M. Tetrahedron Lett. 1993, 34: 855 -
8b
Wang Z.-M.Zhang X.-L.Sharpless KB. Tetrahedron Lett. 1993, 34: 2267 -
8c
Rama Rao AV.Gurjar MK.Joshi SV. Tetrahedron: Asymmetry 1990, 1: 697 - 9
Bevinakatti HS.Banerji AA. J. Org. Chem. 1991, 56: 5372 - 10
Klunder JM.Ko Soo Y.Sharpless KB. J. Org. Chem. 1986, 51: 3710 - 11
Mitsunobu O. Synthesis 1981, 1 - 12
Salazar L.Bermudez JL.Ramirez C.Llama EF.Sinisterra JV. Tetrahedron: Asymmetry 1999, 10: 3507