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Synthesis 2010(2): 349-360
DOI: 10.1055/s-0029-1217139
DOI: 10.1055/s-0029-1217139
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New YorkHeck Reaction in Diols and Cascade Formation of Cyclic Ketals
Weitere Informationen
Received
16 September 2009
Publikationsdatum:
20. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
20. November 2009 (online)
Abstract
The regioselective Heck arylation of butyl vinyl ether in alcohols is utilized for the formation of a variety of cyclic ketals. When carried out in ethylene glycol, propane-1,2-diol, or propane-1,3-diol, the palladium-catalyzed arylation afforded dioxolanes or dioxanes directly. With diols such as glycerol, 3-chloropropane-1,2-diol, and 2-methylpropane-1,3-diol, isolation of the Heck adducts and the use of an acid catalyst for the ketalization were necessary; an efficient phosphoric acid was identified. The procedure presented provides a new pathway for the synthesis of cyclic ketals, particularly those that are functionalized.
Key words
ketals - diols - olefins - Heck reaction - homogeneous catalysis
- 1
Greene TW.Wuts PGM. Greene’s Protecting Groups in Organic Synthesis Wiley; New York: 2006. Chap. 4. p.431 - 2a
Pav O.Barvik I.Budesinsky M.Masojidkova M.Rosenberg I. Org. Lett. 2007, 9: 5469MissingFormLabel - 2b
Yoshioka S.Oshita M.Tobisu M.Chatani N. Org. Lett. 2005, 7: 3697MissingFormLabel - 3
Zapata-Sudo G.Pontes LB.Gabriel D.Mendes TCF.Ribeiro NM.Pinto AC.Trachez MM.Sudo RT. Pharmacol. Biochem. Behav. 2007, 86: 678 - 4
Bisschop M.Merkus J.Scheygrond H.Vancutsem J.Vandekuy A. Eur. J. Obstet. Gynecol. Reprod. Biol. 1979, 9: 253 - 5
Caruso E.D’Arrigo P.Frattini S.Pedrocchi-Fantoni G.Servi S. J. Mol. Catal. B 2001, 11: 427 - 6
Sax M.Fröhlich R.Schepmann D.Wunsch B. Eur. J. Org. Chem. 2008, 6015 - 7
Das BC.Madhukumar AV.Anguiano J.Kim S.Sinz M.Zvyaga TA.Power EC.Ganellin CR.Mani S. Bioorg. Med. Chem. Lett. 2008, 18: 3974 - 8a
Ono F.Inatomi Y.Tada Y.Mori M.Sato T. Chem. Lett. 2009, 38: 96MissingFormLabel - 8b
Perez-Mayoral E.Martin-Aranda RM.Lopez-Peinado AJ.Ballesteros P.Zukal A.Cejka J. Top. Catal. 2009, 52: 148MissingFormLabel - 8c
Doll KM.Erhan SZ. Green Chem. 2008, 10: 712MissingFormLabel - 8d
Gregg BT.Golden KC.Quinn JF. Tetrahedron 2008, 64: 3287MissingFormLabel - 8e
Genta MT.Villa C.Mariani E.Loupy A.Petit A.Rizzetto R.Mascarotti A.Morini F.Ferro M. Int. J. Pharm. 2002, 231: 11MissingFormLabel - 8f
Curini M.Epifano F.Marcotullio MC.Rosati O. Synlett 2001, 1182MissingFormLabel - 8g
Deslongchamps P.Dory YL.Li SG. Helv. Chim. Acta 1996, 79: 41MissingFormLabel - 9a
Kondolff I.Doucet H.Santelli M. Eur. J. Org. Chem. 2006, 765MissingFormLabel - 9b
De SYK.Gibbs RA. Tetrahedron Lett. 2004, 45: 8141MissingFormLabel - 10a
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442MissingFormLabel - 10b
Farina V. Adv. Synth. Catal. 2004, 346: 1553MissingFormLabel - 10c
Blaser HU.Indolese A.Naud F.Nettekoven U.Schnyder A. Adv. Synth. Catal. 2004, 346: 1583MissingFormLabel - 10d
Zapf A.Beller M. Top. Catal. 2002, 19: 101MissingFormLabel - 10e
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009MissingFormLabel - 11a
Hyder Z.Mo J.Xiao JL. Adv. Synth. Catal. 2006, 348: 1699MissingFormLabel - 11b
Larhed M.Hallberg A. J. Org. Chem. 1997, 62: 7858MissingFormLabel - 12a
Whitcombe NJ.Hii KK.Gibson SE. Tetrahedron 2001, 57: 7449MissingFormLabel - 12b
Knowles JP.Whiting A. Org. Biomol. Chem. 2007, 5: 31MissingFormLabel - 12c
Oestreich M. Eur. J. Org. Chem. 2005, 783MissingFormLabel - 12d
Crisp GT. Chem. Soc. Rev. 1998, 27: 427MissingFormLabel - 13a
Berthiol F.Doucet H.Santelli M. Appl. Organomet. Chem. 2006, 20: 855MissingFormLabel - 13b
Park SB.Alper H. Org. Lett. 2003, 5: 3209MissingFormLabel - 13c
Hierso JC.Fihri A.Amardeil W.Meunier P.Doucet H.Santelli M.Donnadieu B. Organometallics 2003, 22: 4490MissingFormLabel - 13d
Calo V.Nacci A.Monopoli A.Detomaso A.Iliade P. Organometallics 2003, 22: 4193MissingFormLabel - 13e
Maeda K.Farrington EJ.Galardon E.John BD.Brown JM. Adv. Synth. Catal. 2002, 344: 104MissingFormLabel - 13f
Schnyder A.Aemmer T.Indolese AE.Pittelkow U.Studer M. Adv. Synth. Catal. 2002, 344: 495MissingFormLabel - 13g
Feuerstein M.Doucet H.Santelli M. Tetrahedron Lett. 2002, 43: 2191MissingFormLabel - 13h
Littke AF.Fu GC. J. Am. Chem. Soc. 2001, 123: 6989MissingFormLabel - 13i
Cabri W.Candiani I. Acc. Chem. Res. 1995, 28: 2MissingFormLabel - 13j
Cabri W.Candiani I.Bedeschi A.Santi R. J. Org. Chem. 1993, 58: 7421MissingFormLabel - 13k
Cabri W.Candiani I.Bedeschi A.Santi R. J. Org. Chem. 1992, 57: 3558MissingFormLabel - 13l
Cabri W.Candiani I.Bedeschi A.Penco S.Santi R. J. Org. Chem. 1992, 57: 1481MissingFormLabel - 13m
Cabri W.Candiani I.Debernardinis S.Francalanci F.Penco S.Santi R. J. Org. Chem. 1991, 56: 5796MissingFormLabel - 13n
Cabri W.Candiani I.Bedeschi A.Santi R. J. Org. Chem. 1990, 55: 3654MissingFormLabel - 13o
Cabri W.Debernardinis S.Francalanci F.Penco S.Santi R. J. Org. Chem. 1990, 55: 350MissingFormLabel - 13p
Daves GD.Hallberg A. Chem. Rev. 1989, 89: 1433MissingFormLabel - 14
Herrmann WA.Brossmer C.Reisinger CP.Riermeier TH.Ofele K.Beller M. Chem. Eur. J. 1997, 3: 1357 - 15a
Amatore C.Godin B.Jutand A.Lemaitre F. Organometallics 2007, 26: 1757MissingFormLabel - 15b
Hansen AL.Skrydstrup T. J. Org. Chem. 2005, 70: 5997MissingFormLabel - 15c
Arefalk A.Larhed M.Hallberg A. J. Org. Chem. 2005, 70: 938MissingFormLabel - 15d
Bengtson A.Larhed M.Hallberg A. J. Org. Chem. 2002, 67: 5854MissingFormLabel - 15e
Olofsson K.Sahlin H.Larhed M.Hallberg A. J. Org. Chem. 2001, 66: 544MissingFormLabel - 15f
Olofsson K.Larhed M.Hallberg A. J. Org. Chem. 2000, 65: 7235MissingFormLabel - 15g
Vallin KSA.Larhed M.Johansson K.Hallberg A. J. Org. Chem. 2000, 65: 4537MissingFormLabel - 15h
Albert K.Gisdakis P.Rosch N. Organometallics 1998, 17: 1608MissingFormLabel - 15i
Larhed M.Hallberg A. J. Org. Chem. 1996, 61: 9582MissingFormLabel - 15j
Ozawa F.Kubo A.Hayashi T. J. Am. Chem. Soc. 1991, 113: 1417MissingFormLabel - 15k
Sato Y.Sodeoka M.Shibasaki M. Chem. Lett. 1990, 1953MissingFormLabel - 16a
Surawatanawong P.Fan Y.Hall MB. J. Organomet. Chem. 2008, 693: 1552MissingFormLabel - 16b
Amatore C.Godin B.Jutand A.Lemaitre F. Chem. Eur. J. 2007, 13: 2002MissingFormLabel - 16c
Deeth RJ.Smith A.Brown JM. J. Am. Chem. Soc. 2004, 126: 7144MissingFormLabel - 16d
Hahn C. Chem. Eur. J. 2004, 10: 5888MissingFormLabel - 16e
von Schenck H.Akermark B.Svensson M. J. Am. Chem. Soc. 2003, 125: 3503MissingFormLabel - 16f
Hii KK.Claridge TDW.Brown JM.Smith A.Deeth RJ. Helv. Chim. Acta 2001, 84: 3043MissingFormLabel - 16g
Deeth RJ.Smith A.Hii KK.Brown JM. Tetrahedron Lett. 1998, 39: 3229MissingFormLabel - 17a
Andersson CM.Hallberg A. J. Org. Chem. 1989, 54: 1502MissingFormLabel - 17b
Andersson CM.Hallberg A. J. Org. Chem. 1988, 53: 2112MissingFormLabel - 18a
Hansen AL.Skrydstrup T. Org. Lett. 2005, 7: 5585MissingFormLabel - 18b
Tu T.Hou XL.Dai LX. Org. Lett. 2003, 5: 3651MissingFormLabel - 18c
Barcia C.Cruces J.Estevez JC.Estevez RJ.Castedo L. Tetrahedron Lett. 2002, 43: 5141MissingFormLabel - 18d
Ludwig M.Stromberg S.Svensson M.Akermark B. Organometallics 1999, 18: 970MissingFormLabel - 19a
Mo J.Ruan JW.Xu LJ.Hyder Z.Saidi O.Liu SF.Pei W.Xiao JL. J. Mol. Catal. A 2007, 261: 267MissingFormLabel - 19b
Mo J.Xiao JL. Angew. Chem. Int. Ed. 2006, 45: 4152MissingFormLabel - 19c
Liu SF.Berry N.Thomson N.Pettman A.Hyder Z.Mo J.Xiao JL. J. Org. Chem. 2006, 71: 7467MissingFormLabel - 19d
Mo J.Xu LJ.Ruan JW.Liu SF.Xiao JL. Chem. Commun. 2006, 3591MissingFormLabel - 19e
Mo J.Xu LJ.Xiao JL. J. Am. Chem. Soc. 2005, 127: 751MissingFormLabel - 19f
Xu LJ.Chen WP.Ross J.Xiao JL. Org. Lett. 2001, 3: 295MissingFormLabel - 20a
Hyder Z.Ruan JW.Xiao JL. Chem. Eur. J. 2008, 14: 5555MissingFormLabel - 20b
Xu D.Liu ZH.Tang WJ.Xu LJ.Hyder Z.Xiao JL. Tetrahedron Lett. 2008, 49: 6104MissingFormLabel - 20c
Liu ZH.Xu D.Tang WJ.Xu LJ.Mo J.Xiao JL. Tetrahedron Lett. 2008, 49: 2756MissingFormLabel - 20d
He T.Tao X.Wu X.Cai L.Pike VW. Synthesis 2008, 887MissingFormLabel - 21a
Bodkin JA.Bacskay GB.McLeod MD. Org. Biomol. Chem. 2008, 6: 2544MissingFormLabel - 21b
Jones MC.Marsden SP. Org. Lett. 2008, 10: 4125MissingFormLabel - 22
Quin LD. A Guide to Organophosphorus Chemistry Wiley; New York: 2000.