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Synthesis 2003(9): 1324-1328
DOI: 10.1055/s-2003-40210
DOI: 10.1055/s-2003-40210
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Facile Generation of Alkenes and Dienes from Tosylates
Further Information
Received
6 March 2003
Publication Date:
24 June 2003 (online)
Publication History
Publication Date:
24 June 2003 (online)
Abstract
Several aldol products resulting from Evans aldol reactions were converted to primary alcohols. After conversion to the corresponding tosylates, heating with NaI and DBU in dimethoxyethane (glyme) effected clean elimination to the terminal olefin. This simple one-pot procedure was applied to other tosylates and a tosylate derived from a homoallylic alcohol. The latter gave rise to a diene.
Key words
aldol reactions - alkenes - eliminations
-
1a
Still WC.Barrish JC. J. Am. Chem. Soc. 1983, 105: 2487 -
1b
Houk KN.Rondan NG.Wu Y.-D.Metz JT.Paddon-Row MN. Tetrahedron 1984, 40: 2257 -
1c
Evans DA.Fu GC.Hoveyda AH. J. Am. Chem. Soc. 1988, 110: 6917 -
1d
Harada T.Matsuda Y.Wada I.Uchimura J.Oku A. J. Chem. Soc., Chem. Commun. 1990, 21 -
1e
Burgess K.Cassidy J.Ohlmeyer MJ. J. Org. Chem. 1991, 56: 1020 - 2
Schinzer D.Limberg A.Böhm O. Chem.-Eur. J. 1996, 2: 1477 -
3a
Hayashi M.Inoue T.Miyamoto Y.Oguni N. Tetrahedron 1994, 50: 4385 -
3b
Nicolaou KC.Ritzén A.Namoto K. Chem. Commun. 2001, 1523 ; and references therein - 4
Schinzer D.Bauer A.Schieber J. Chem.-Eur. J. 1999, 5: 2492 - For some representative examples, see:
-
5a
Hakimelahi GH.Mei N.-W.Moosavi-Movahedi AA.Davari H.Hakimelahi S.King K.-Y.Hwu JR.Wen Y.-S. J. Med. Chem. 2001, 44: 1749 -
5b
Werschkun B.Thiem J. Angew. Chem., Int. Ed. Engl. 1997, 36: 2793 ; Angew. Chem.; 1997, 109, 2905 -
5c
Wang W.Zhang Y.Zhou H.Bleriot Y.Sinay P. Eur. J. Org. Chem. 2001, 1053 -
5d
Sato K.Sakuma S.Nakamura Y.Yoshimura J.Hashimoto H. Chem. Lett. 1991, 17 -
5e
Jokic M.Skaric V. J. Chem. Soc., Perkin Trans. 1 1989, 757 -
5f
Sinclair HB. Carbohydr. Res. 1988, 181: 115 - 6
Sato K.-i.Kubo N.Takada R.Sakuma S. Bull. Chem. Soc. Jpn. 1993, 66: 1156 - 7
Kabalka GW.Varma M.Varma RS.Srivastava PC.Knapp FF. J. Org. Chem. 1986, 51: 2386 -
8a
Gage JR.Evans DA. Org. Synth. 1989, 68: 83 -
8b
Gage JR.Evans DA. Org. Synth. 1989, 68: 77 - 9 Review:
Arya P.Qin H. Tetrahedron 2000, 56: 917 - 10
Prashad M.Kim H.-Y.Lu Y.Liu Y.Har D.Repic O.Blacklock TJ.Giannousis P. J. Org. Chem. 1999, 64: 1750 -
11a
Jenmalm A.Berts W.Li Y.-L.Luthman K.Csoeregh I.Hacksell U. J. Org. Chem. 1994, 59: 1139 -
11b
Berque I.Le Ménez P.Razon P.Mahuteau J.Férézou J.-P.Pancrazi A.Ardisson J.Brion J.-D. J. Org. Chem. 1999, 64: 373 -
11c
Enders D.Kirchhoff JH. Synthesis 2000, 2099 - 12
Crimmins MT.King BW.Tabet EA.Chaudhary K. J. Org. Chem. 2001, 66: 894 - 13
Bauer M.Maier ME. Org. Lett. 2002, 4: 2205 - 14
Hunter R.Hinz W.Richards P. Tetrahedron Lett. 1999, 40: 3643 -
15a
Koto S.Morishima N.Mori Y.Tanaka H.Hayashi S.Iwai Y.Zen S. Bull. Chem. Soc. Jpn. 1987, 60: 2301 -
15b
Umemura K.Matsuyama H.Kobayashi M.Kamigata N. Bull. Chem. Soc. Jpn. 1989, 62: 3026 - 16
Mori K.Harashima S. Liebigs Ann. Chem. 1993, 391 - 17
Matsuda F.Kito M.Sakai T.Ojkada N.Miyashita M.Shirahama H. Tetrahedron 1999, 55: 14369 -
18a
Evans DA.Chapman KT.Bisaha J. J. Am. Chem. Soc. 1988, 110: 1238 -
18b
Thom C.Kocienski P. Synthesis 1992, 582 -
18c
Rueck K.Kunz H. Synthesis 1993, 1018 -
18d
Ho G.-J.Mathre DJ. J. Org. Chem. 1995, 60: 2271 -
18e
Raw AS.Jang EB. Tetrahedron 2000, 56: 3285 - For related aldol reactions, see:
-
19a
Evans DA.Sjogren EB.Bartroli J.Dow RL. Tetrahedron Lett. 1986, 27: 4957 -
19b
McGarvey GJ.Mathys JA.Wilson KJ. J. Org. Chem. 1996, 61: 5704 -
21a
Langer F.Schwink L.Devasagayaraj A.Chavant P.-Y.Knochel P. J. Org. Chem. 1996, 61: 8229 -
21b
Youn J.-H.Lee J.Cha JK. Org. Lett. 2001, 3: 2935 -
22a
Semeria D.Philippe M.Delaumeny JM.Sepulchre AM.Gero SD. Synthesis 1983, 710 -
22b
Boyer F.-D.Lallemand J.-Y. Tetrahedron 1994, 50: 10443 - 23
Ferrier RJ.Middleton S. Chem. Rev. 1993, 93: 2779 - 24
Hayashi T.Iwamura H.Uozumi Y.Matsumoto Y.Ozawa F. Synthesis 1994, 526 -
25a
Soundarajan R.Li G.Brown HC. J. Org. Chem. 1996, 61: 100 -
25b
Xiang AX.Watson DA.Ling T.Theodorakis EA. J. Org. Chem. 1998, 63: 6774
References
Phukan P.; Sasmal, S.; Maier, M. E. Eur. J. Org. Chem. 2003, 1733.