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Synthesis 2005(17): 2838-2844
DOI: 10.1055/s-2005-872178
DOI: 10.1055/s-2005-872178
PAPER
© Georg Thieme Verlag Stuttgart · New YorkRapid and Solvent-Free Synthesis of Homoallyl or Homopropargyl Alcohols Mediated by Zinc Powder
Weitere Informationen
Received
20 April 2005
Publikationsdatum:
16. August 2005 (online)
Publikationsverlauf
Publikationsdatum:
16. August 2005 (online)
Abstract
A rapid and efficient procedure for the solvent-free synthesis of homoallylic and homopropargyl alcohols has been achieved by zinc-mediated Barbier-type reaction of carbonyl compounds at room temperature.
Key words
zinc powder - solvent-free - homoallylic alcohol - homopropargyl alcohol - carbonyl compounds
- 1a
Nicolaou KC.Kim DW.Baati R. Angew. Chem. Int. Ed. 2002, 41: 3701 - 1b
Nicolaou KC.Ninkovic S.Sarabia F.Vourloumis D.He Y.Valllberg H.Finlay MRV.Yang Z. J. Am. Chem. Soc. 1997, 119: 7974 - 1c
Bartlett PA. Tetrahedron 1980, 36: 3 - 1d
Paterson I.Mansuri MM. Tetrahedron 1985, 41: 3569 - 1e
Germay O.Kumar N.Thomas EJ. Tetrahedron Lett. 2001, 42: 4969 - 1f
Hayward CM.Yohannes D.Danishefsky SJ. J. Am. Chem. Soc. 1993, 115: 9345 - 2a
Roush WR. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I.Heathcock CH. Pergamon Press; Oxford: 1991. p.1 - 2b
Yamamoto Y.Asao N. Chem. Rev. 1993, 93: 2207 - 3a
Li CJ. Chem. Rev. 1993, 93: 2023 - 3b
Lubineau A.Auge J.Queneau Y. Synthesis 1994, 741 - 3c
Li CJ. Tetrahedron 1996, 52: 5643 - 4a
Yanagisawa A.Habaue S.Yamamoto H. J. Org. Chem. 1989, 54: 5198 - 4b
Nicolaou KC.Skokotas G.Furuya S.Suemune H.Nicolaou DC. Angew. Chem., Int. Ed. Engl. 1990, 29: 1064 - 4c
Fryhle CB.Williard PG.Rybak CM. Tetrahedron Lett. 1992, 33: 2327 - 4d
Hirama M.Tokuda M.Fujiwara K. Synlett 1991, 651 - 4e
Lee AS.-Y.Cheng R.-Y.Pan O.-G. Tetrahedron Lett. 1997, 38: 443 - 5
Zhang L.-J.Mo X.-S.Huang Y.-Z. J. Organomet. Chem. 1994, 471: 77 - 6
Brown HC.Khire UR.Narla G.Racherla US. J. Org. Chem. 1995, 60: 544 - 7
Araki S.Ito H.Butsugan Y. J. Organomet. Chem. 1988, 347: 5 - 8
Hojo M.Sakuragi R.Okabe S.Hosomi A. Chem. Commun. 2001, 357 - 9a
Araki S.Ito H.Butsugan Y. J. Org. Chem. 1988, 53: 1833 - 9b
Isaac MB.Chan T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003 - 10
Hojo M.Harada H.Ito H.Hosomi A. Chem. Commun. 1997, 2077 - 11
Mukaiyama T.Harada T. Chem. Lett. 1981, 621 - 12
Tanaka H.Hamatani T.Yamashita S.Torii S. Chem. Lett. 1986, 1461 - 13a
Ishiguro M.Ikeda N.Yamamoto H. J. Org. Chem. 1982, 47: 2225 - 13b
Nakagawa T.Kasatkin A.Sato F. Tetrahedron Lett. 1995, 36: 3207 - 14a
Multzer J.Altenbach HJ.Braun M.Krohn K.Reissig HU. Organic Synthesis Highlights VCH; Weinheim Germany: 1991. p.71 - 14b
Grieco PA. Aldrichimica Acta 1991, 24: 59 - 15a
Killinger TA.Boughton NA.Runge TA.Wolinsky J. J. Organomet. Chem. 1977, 124: 131 - 15b
Makosza M.Grela K. Synth. Commun. 1996, 26: 2935 - 15c
Einhorn C.Luche JL. J. Organomet. Chem. 1987, 322: 177 - 15d
Wilson SR.Guazzaroni ME. J. Org. Chem. 1989, 54: 3087 - 15e
Oda Y.Matsuo S.Saito K. Tetrahedron Lett. 1992, 33: 97 - 15f
Lee AS.-Y.Chang Y.-T.Wang S.-H.Chu S.-F. Tetrahedron Lett. 2002, 43: 8489 - 15g
Zhou CL.Zhou YQ.Jiang JY.Zh X.Wang ZY.Zhang JH.Wu JH.Yin H. Tetrahedron Lett. 2004, 45: 5537 - 15h
Resende GO.Aguiar LCS.Antunes OAC. Synlett 2005, 119 - 16a
Anastas PT.Warner JC. Green Chemistry: Theory and Practice Oxford University Press; Oxford New York: 1998. - 16b
Yochida M.Mariano PS. J. Org. Chem. 1996, 61: 4439 - 17
Holbrey JD.Seddon KR. J. Chem. Soc. Dalton Trans. 1999, 99: 2701 - 18a
Chan TH.Yang Y. J. Am. Chem. Soc. 1999, 121: 3228 - 18b
Li CJ.Chan TH. Organic Reactions in Aqueous Media John Wiley & Sons; New York: 1997. - 19a
Oakes RS.Heppenstall TJ.Shezad N.Clifford AA.Rayner CM. Chem. Commun. 1999, 1459 - 19b
Shezad N.Clifford AA.Rayner CM. Tetrahedron Lett. 2001, 42: 323 - 19c
Darr JA.Poliakoff M. Chem. Rev. 1999, 99: 495 - 20
Roberts BA.Cave GWV.Raston CJ.Scott JL. Green Chem. 2000, 3: 280 - 21
Cave GW.Raston CJ.Scott JL. Chem. Commun. 2001, 2159 - 22
Tanaka K.Toda F. Chem. Rev. 2000, 100: 1025 - 23a
Wang J.-X.Fu Y.Hu Y. Angew. Chem. Int. Ed. 2002, 41: 2757 - 23b
Wang J.-X.Fu Y.Hu Y.Wang K. Synthesis 2003, 1506 - 23c
Hu YL.Wang J.-X.Li W. Chem. Lett. 2001, 2: 174 - 24a
Andrews PC.Peatt AC.Raston CL. Green Chem. 2001, 3: 313 - 24b
Andrews PC.Peatt AC.Raston CL. Tetrahedron Lett. 2002, 43: 7541 - 25
Gomes P.Gosmini C.Perichon J. Synthesis 2003, 1909 - 26
Jang T.-S.Keum G.Kang SB.Chung BY.Kim Y. Synthesis 2003, 775 - 27
Wang ZY.Yuan SZ.Li CJ. Tetrahedron Lett. 2002, 43: 5097 - 28
Lee AS.-Y.Chu S.-F.Chang Y.-T.Wang S.-H. Tetrahedron Lett. 2004, 45: 1551 - 29a
Hansen SW.Spawn TD.Burton DJ. J. Fluorine Chem. 1987, 37: 415 - 29b
Heinze PL.Burton DJ. J. Org. Chem. 1988, 53: 2714 - 30a
Knochel P.Yeh MCP.Berk SC.Talbert J. J. Org. Chem. 1988, 53: 2390 - 30b
Erdik E. Tetrahedron 1987, 43: 2203 - 30c
Picotin G.Miginiac P. J. Org. Chem. 1987, 52: 4796 - 30d
Picotin G.Miginiac P. Tetrahedron Lett. 1987, 28: 4551 - 31
Kurono N.Honda E.Komatsu F.Orito K.Tokuda M. Tetrahedron 2004, 60: 1791 - 32
Schumann H.Kaufmann J.Dechert S.Schmalz H.-G. Tetrahedron Lett. 2002, 43: 3507 - 33
Yasuda M.Fujibayashi T.Baba A. J. Org. Chem. 1998, 63: 6401 - 34
Kowaski CJ.Dung J.-S. J. Am. Chem. Soc. 1980, 102: 7950 - 35
Riediker M.Duthaler RO. Angew. Chem., Int. Ed. Engl. 1989, 28: 494 ; Riediker, M.; Duthaler, R. O. Angew. Chem. 1989, 101, 488 - 36a
Singh S.Kumar S.Chimni SS. Tetrahedron: Asymmetry 2002, 13: 2679 - 36b
Wang ZG.Kianga P.Verkade JG. J. Org. Chem. 1999, 64: 6459 - 37
Daudé G.Pereyre M. J. Organomet. Chem. 1980, 190: 43 - 38
Iyoda M.Kanao Y.Nishizaki M.Oda M. Bull. Chem. Soc. Jpn. 1989, 62: 3380 - 39
Zheng YF.Bao WL.Zhang YM. Synth. Commun. 2000, 30: 3517 - 40
Michelot D. Synth. Commun. 1989, 19: 1705 - 41a
Viola A.Proverb RJ.Yates BL.Larrahondo J. J. Am. Chem. Soc. 1973, 95: 3609 - 41b
Shim J.-G. J. Organomet. Chem. 1999, 588: 20