Subscribe to RSS
DOI: 10.1055/s-2005-918482
Diastereoselective Friedel-Crafts Cyclization Reactions to 2-Substituted 1-Phenyl-1,2,3,4-tetrahydronaphthalenes
Publication History
Publication Date:
14 November 2005 (online)
Abstract
1′-Substituted 1-phenyl-1-(3′-phenylprop-1′-yl)alkenes, 1-substituted 2-methyl-4-phenylbutanols, and 2,5-diphenyl-3-methyl-2-pentanol were synthesized from known starting materials. These compounds and the known epoxide 2-phenethyl-3-phenyloxirane were subjected to Brønsted or Lewis acid promoted Friedel-Crafts cycloalkylations, which proceeded with almost perfect diastereoselectivity (dr >95:5). For the cyclization reaction to tetralins (five examples) trifluoromethane sulfonic acid proved to be the reagent of choice (91-98% yield). The diastereoselective cyclization of epoxide 2-phenethyl-3-phenyloxirane to trans-1,2,3,4-tetrahydro-1-phenylnaphth-2-ol was accompanied by side reactions and the yield was lower (45%). The reactions occurred stereoconvergently, i.e. a mixture of diastereoisomers led to a single diastereomeric product under kinetic control. An explanantion for the observed diastereoselectivity is put forward.
Key words
carbocations - stereoselective synthesis - electrophilic aromatic substitutions - alkylations - regioselectivity
- 1
Newis NG.Davin LB. In Comprehensive Natural Product Chemistry Vol. 1:Barton D.Nakanishi K. Elsevier; Amsterdam: 1999. p.639 - Examples:
- 2a
Sumichika H.Sakata K.Sato N.Takeshita S.Ishibuchi S.Nakamura M.Kamahori T.Ehara S.Itoh K.Ohtsuka T.Ohbora T.Mishina T.Komatsu H.Naka Y. J. Biol. Chem. 2002, 277: 49403 - 2b
Fourmaintraux E.Depreux P.Lesieur D.Guardiola-Lemaitre B.Bennejean C.Delagrange P.Howell HE. Bioorg. Med. Chem. 1998, 6: 9 - 2c
Hartmann RW.Frotscher M.Ledergerber D.Waechter GA.Gruen GL.Segejew TF. Arch. Pharm. 1996, 329: 251 - 3
Barclay LRC. In Friedel-Crafts and Related Reactions Vol. 2:Olah GA. John Wiley & Sons Inc.; New York: 1964. p.785 - 4a
Mal SK.Kar GK.Ray JK. Tetrahedron 2004, 60: 2805 - 4b
Corey EJ.Luo G.Lin LS. Angew. Chem. Int. Ed. 1998, 37: 1126 - 4c
Gosh S.Gosh AK.Ghatak UR. Synth. Commun. 1992, 22: 553 - 4d
Gosh S.Banik BK.Ghatak UR. J. Chem. Soc., Perkin Trans. 1 1991, 3189 - 4e
Bright ST.Coxon JM.Steel PJ. J. Org. Chem. 1990, 55: 1338 - 4f
Banik BK.Ghosh S.Ghatak UR. Tetrahedron 1988, 44: 6947 - 4g
Davis BR.Hinds MG.Johnson SJ. Aust. J. Chem. 1985, 38: 1815 - 4h
Kusumi T.Ohno N.Kakisawa H. Bull. Chem. Soc. Jpn. 1975, 48: 96 - 4i
Adkins H.Hager GF. J. Am. Chem. Soc. 1949, 71: 2965 - 5a
Nagumo S.Miyoshi I.Akita H.Kawahara N. Tetrahedron Lett. 2002, 43: 2223 - 5b
Elings JA.Downing RS.Sheldon RA. Eur. J. Org. Chem. 1999, 837 - 5c
Medarde M.Ramos AC.Caballero E.López JL. Tetrahedron Lett. 1998, 39: 2001 - 5d
Angle SR.Louie MS. J. Org. Chem. 1991, 56: 2853 - 5e
Taylor SK.Davisson ME.Hissom BR.Brown SL.Pristach HA.Schramm SB.Harvey SM. J. Org. Chem. 1987, 52: 425 - 5f
Ganeshpure PA.Stevenson R. J. Chem. Soc., Perkin Trans. 1 1981, 1681 - 5g
Brown E.Loriot M.Robin J.-P. Tetrahedron Lett. 1979, 20: 1389 - 5h
Ziegler FE.Schwartz JA. J. Org. Chem. 1978, 43: 985 - 5i
Khalaf AA.Roberts RM. J. Org. Chem. 1972, 37: 4227 - 6
Lednicer D.Emmert DE.Lyster SC.Duncan GW. J. Med. Chem. 1969, 12: 881 - 7
Lindström UM.Somfai P. Synthesis 1997, 109 - 8 For a diastereoselective Friedel-Crafts cycloalkylation to a 1,2,3,4-tetrahydroisoquinoline,
see:
Coote SJ.Davies SG. J. Chem. Soc., Chem. Commun. 1988, 648 - 9 Preliminary communication:
Mühlthau F.Schuster O.Bach T. J. Am. Chem. Soc. 2005, 127: 9348 - 10
Rodriguez AL.Bunlaksananusorn T.Knochel P. Org. Lett. 2000, 2: 3285 - 11a
Miyaoka H.Shida H.Yamada N.Mitome H.Yamada Y. Tetrahedron Lett. 2002, 43: 2227 - 11b
Appel R. Angew. Chem. Int. Ed. 1975, 14: 801 - 12a
Tamura Y.Bayomi SM.Sumoto K.Ikeda M. Synthesis 1977, 693 - 12b
Satoh T.Kobayashi S.Nakanishi S.Horiguchi K.Irisa S. Tetrahedron 1999, 55: 2515 - 13a
Hon Y.-S.Lu L.Chang R.-C.Lin S.-W.Sun P.-P.Lee C.-F. Tetrahedron 2000, 56: 9269 - 13b
Snider BB.Jackson AC. J. Org. Chem. 1983, 48: 1471 - 14 Review:
Hughes DL. Chem. React. 1992, 42: 335 - 15
Maehr H. J. Chem. Educ. 1985, 62: 114 - 16a
Lee NR.Lee JI. Synth. Commun. 1999, 29: 1249 - 16b
Donkor IO.Li H.Queener SF. Eur. J. Med. Chem. 2003, 38: 605 - 17a
Alcock NJ.Mann I.Peach P.Wills M. Tetrahedron: Asymmetry 2002, 13: 2485 - 17b
Wyrick SD.Booth RG.Myers AM.Owens CE.Bucholtz EC.Hooper PC.Kula NS.Baldessarini RJ.Mailman RB. J. Med. Chem. 1995, 38: 3857 - 17c
Laus G.Tourwé D.Van Binst G. Heterocycles 1984, 22: 311 - 19 Review:
Hoffmann RW. Chem. Rev. 1989, 89: 1841 - 20 For a related phenomenon, see:
Shimamoto K.Ohfune Y. Tetrahedron Lett. 1988, 29: 5177
References
Mühlthau, F., Herdtweck, E., Bach, T., unpublished results.