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DOI: 10.1055/s-2002-19297
A Convenient Method for the Synthesis of Terminal (E)-1,3-Dienes
Publikationsverlauf
Publikationsdatum:
04. August 2004 (online)
Abstract
Lithiated allylic phosphonates undergo efficient olefination reactions with a variety of aldehydes in the presence of HMPA to give terminal 1,3-dienes with high selectivity for the E-isomer. This method is general and procedurally simple.
Key words
aldehydes - alkenation - phosphorus - Wittig reactions - ylides
- 1
Wang Y.Arif AM.West FG. J. Am. Chem. Soc. 1999, 121: 876 -
2a
Bull JR.Gordon R.Hunter R. J. Chem. Soc., Perkin Trans. 1 2000, 3129 -
2b
Craig D.Geach NJ.Pearson CJ.Slawin AMZ.White AJP.Williams DJ. Tetrahedron 1995, 51: 6071 -
2c
Wulff WD.Powers TS. J. Org. Chem. 1993, 58: 2381 -
2d
Smith DA.Houk KN. Tetrahedron Lett. 1991, 32: 1549 -
2e
Segi M.Takahashi M.Nakajima T.Suga S.Sonoda N. Synth. Commun. 1989, 19: 2431 -
2f
Oppolzer W.Dupuis D. Tetrahedron Lett. 1985, 26: 5437 -
2g
Roush WR.Hall SE. J. Am. Chem. Soc. 1981, 103: 5200 - For recent studies on synthesis of 1,3-dienes using transition metal catalysts, see:
-
3a
Kinoshita A.Sakakibara N.Mori M. Tetrahedron 1999, 55: 8155 -
3b
Karlstrom ASE.Itami K.Backvall J.-E. J. Org. Chem. 1999, 64: 1745 - 4
Claus RE.Schreiber SL. Org. Synth. 1985, 64: 150 - 5
Tsai DJS.Matteson DS. Tetrahedron Lett. 1981, 22: 2751 -
6a
Sato F.Suzuki Y.Sato M. Tetrahedron Lett. 1982, 23: 4589 -
6b
Yamamoto H.Ikeda Y. Bull. Chem. Soc. Jpn. 1986, 59: 657 -
7a
Maeta H.Hasegawa T.Suzuki K. Synlett 1993, 341 -
7b
Maeta H.Suzuki K. Tetrahedron Lett. 1992, 33: 5969 - 8
Lawrence NJ. In Preparation of AlkenesWilliams JMJ. Oxford University Press; Oxford: 1996. p.19 - 9
Schlosser M. Top. Stereochem. 1970, 5: 1 - 10
Vedejs E.Huang W.-F. J. Org. Chem. 1984, 49: 210 - 11
Tamura R.Saegusa K.Kakihana M.Oda D. J. Org. Chem. 1988, 53: 2723 - 12
Ikeda Y.Ukai J.Ikeda N.Yamamoto H. Tetrahedron 1987, 43: 723 - For representative applications of Yamamoto’s protocol in synthesis, see:
-
13a
Cramer CJ.Harmata M.Rashatasakohn P. J. Org. Chem. 2001, 66: 5641 -
13b
Benbow JW.Katoch R.Martinez BL.Shetzline SB. Tetrahedron Lett. 1997, 38: 4017 -
13c
Stork G.West F.Lee HY.Isaacs RCA.Manabe S. J. Am. Chem. Soc. 1996, 118: 10660 -
13d
Toyota M.Nishikawa Y.Fukumoto K. Tetrahedron 1996, 52: 10347 -
13e
Lautens M.Tam W.Lautens JC.Edwards LG.Crudden CM.Smith AC. J. Am. Chem. Soc. 1995, 117: 6863 -
13f
Takacs JM.Weidner JJ.Newsome PW.Takacs BE.Chidambaram R.Shoemaker R. J. Org. Chem. 1995, 60: 3473 - 15
Schlosser M.Liu R.-Q. Synlett 1996, 1197 - Reviews:
-
16a
Kulkarni YS. Aldrichimica Acta 1990, 23: 39 -
16b
Maryanoff B.Reitz AB. Chem. Rev. 1989, 89: 863 - Examples:
-
17a
Fettes K.McQuire L.Murray SW. J. Chem. Soc., Perkin Trans. 1 1995, 2123 -
17b
Roush WR.Sciotti RJ. J. Am. Chem. Soc. 1994, 116: 6457 -
17c
Janecki T. Synth. Commun. 1993, 23: 641 -
Pattenden G.Weedon BCL. J. Chem. Soc. (C) 1968, 1984 -
18a
Platonov AYu.Sivakov AA.Chistokletov VN.Maiorova ED. Russ. Chem. Bull. 1999, 48: 367 -
18b
Villemin D.Simeon F.Decreus H.Jaffres P.-A. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 133: 209 -
18c
Malet R.Moreno-Manas M.Pleixats R. Synth. Commun. 1992, 22: 2219 -
18d
Khachatryan RA.Ovsepyan SA.Indzhikyan MG. J. Gen. Chem. USSR (Engl.Transl.) 1987, 57: 1524 -
18e
Bride MH.Cummings WAW.Pickles W. J. Appl. Chem. 1961, 11: 352 - Examples:
-
19a
BuLi (1.2 equiv) was added to 5a and HMPA (2.4 equiv) in THF at -78 °C, and the solution was stirred for 1 h. Aldehyde 2 in THF was added dropwise and the reaction mixture was allowed to warm to r.t.; yield <20%.
-
19b
BuLi (1.2 equiv) was added to 5a in THF at -78 °C, and the solution was stirred for 1 h. Aldehyde 2 and HMPA (2.4 equiv) in THF were added dropwise and the reaction mixture was allowed to warm to r.t.; yield: 42%.
-
20a
Muller EL.Modro TA. Heteroat. Chem. 1994, 5: 287 -
20b
Gerber JP.Modro TA. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 88: 99 -
20c
Modro TA.Muller EL. Bull. Soc. Chim. Fr. 1993, 130: 668 -
21a
Mphahlete MJ.Modro TA. J. Chem. Soc., Perkin Trans. 1 1996, 2261 -
21b
Phillips AMMM.Modro TA. J. Chem. Soc., Perkin Trans. 1 1991, 1875 -
21c
Phillips AMMM.Modro TA. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55: 41 -
22a
Carlier PR.Lo CWS. J. Am. Chem. Soc. 2000, 122: 12819 -
22b
Leung SS.-W.Streitwieser A. J. Org. Chem. 1999, 64: 3390 -
22c
Reich HJ.Sikorski WH. J. Org. Chem. 1999, 64: 14 - 23
Probst MF.Modro AM.Modro TA. Can. J. Chem. 1997, 75: 1131 -
24a
Clasby MC.Craig D.Slawin AMZ.White AJP.Williams DJ. Tetrahedron 1995, 1509 -
24b
Goldberg DR.Hansen JA.Giguerre RJ. Tetrahedron Lett. 1993, 34: 8003 -
24c
Kozikowski AP.Hiraga K.Springer JP.Wang BC.Xu Z.-B. J. Am. Chem. Soc. 1984, 106: 1845 - 25
Audin P.Doutheau A.Gore J. Bull. Soc. Chim. Fr. 1984, 11: 297 - 26
Kojima R.Yamashita T.Tanabe K.Shiragami T.Yasuda M.Shima K. J. Chem. Soc., Perkin Trans. 1 1997, 217 - 27
Tamura R.Saegusa K.Kakihana M.Oda D. J. Org. Chem. 1988, 53: 2723
References
While this work was underway, Schlosser and Liu reported a highly stereoselective synthesis of (E)-1,3-dienes with allylphosphonates. [15] However, experimental details were not provided for the optimized conditions using unsubstituted diethyl allylphosphonate with the straight-chain aldehyde nonanal (NaH activated with LiAlH4), and we could not consistently reproduce the reported results (74% yield, 99:1 E/Z).