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
References
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
18 Mühlthau, F., Herdtweck, E., Bach, T., unpublished results.
19 Review: Hoffmann RW.
Chem. Rev.
1989,
89:
1841
20 For a related phenomenon, see: Shimamoto K.
Ohfune Y.
Tetrahedron Lett.
1988,
29:
5177
