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Synthesis 2011(13): 2073-2078
DOI: 10.1055/s-0030-1260045
DOI: 10.1055/s-0030-1260045
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkN-Heterocyclic Carbene Catalyzed Hydrophosphonylation of Aldehydes
Further Information
Received
21 February 2011
Publication Date:
13 May 2011 (online)
Publication History
Publication Date:
13 May 2011 (online)
Abstract
N-Heterocyclic carbene catalyzed Pudovik-type reaction of dimethyl trimethylsilyl phosphite and aldehydes for the construction of carbon-phosphorus bonds have been developed, providing α-hydroxyphosphonates in moderate to excellent yield.
Key words
N-heterocyclic carbene - Pudovik-type reaction - α-hydroxyphosphonates - aldehydes - C-P bond
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Arduengo AJ.Harlow RL.Kline M. J. Am. Chem. Soc. 1991, 113: 361 - For recent reviews, see:
- 1b
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 - 1c
Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506 - 1d
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 - 1e
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 - 1f
Nair V.Vellalath S.Babu BP. Chem. Soc. Rev. 2008, 37: 2691 - 2a
Ugai T.Tanaka S.Dokawa S. J. Pharm. Soc. Jpn. 1943, 63: 269 - 2b
Enders D.Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743 - 2c
Enders D.Niemeier O.Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 - 2d
Takikawa H.Hachisu Y.Bode JW.Suzuki K. Angew. Chem. Int. Ed. 2006, 45: 3492 - 2e
Enders D.Han J. Tetrahedron: Asymmetry 2008, 19: 1367 - 3a
Stetter H.Schreckenberg M. Angew. Chem. Int. Ed. Engl. 1973, 12: 81 - 3b
Kerr MS.Rovis T. Synlett 2003, 1934 - 3c
Kerr MS.Rovis T. J. Am. Chem. Soc. 2004, 126: 8876 - 3d
Nakamura T.Hara O.Tamura T.Makino K.Hamada Y. Synlett 2005, 155 - 3e
Mattson AE.Zuhl AM.Reynolds TE.Scheidt KA. J. Am. Chem. Soc. 2006, 128: 4932 - 3f
Dirocco DA.Oberg KM.Dalton DM.Rovis T. J. Am. Chem. Soc. 2009, 131: 10872 - 4a
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205 - 4b
Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370 - 4c
Burstein C.Tschan S.Xie X.Glorius F. Synthesis 2006, 2418 - 4d
Nair V.Vellalath S.Poonoth M.Suresh E. J. Am. Chem. Soc. 2006, 128: 8736 - 4e
Chiang P.-C.Kaeobamrung J.Bode JW. J. Am. Chem. Soc. 2007, 129: 3520 - 4f
David BC.Raup DEA.Scheidt KA. J. Am. Chem. Soc. 2010, 132: 5345 - 5a
Nyce GW.Lamboy JA.Connor EF.Waymouth RM.Hedrick JL. Org. Lett. 2002, 4: 3587 - 5b
Grasa GA.Kissling RM.Nolan SP. Org. Lett. 2002, 4: 3583 - 5c
Grasa GA.Singh SM.Nolan SP. Synthesis 2004, 971 - 5d
Kano T.Sasaki K.Maruoka K. Org. Lett. 2005, 7: 1347 - 5e
Zeng T.-Q.Song G.-H.Li C.-J. Chem. Commun. 2009, 41: 6249 - 6a
Connor EF.Nyce GW.Myers M.Möck A.Hedrick JL. J. Am. Chem. Soc. 2002, 124: 914 - 6b
Nyce GW.Glauser T.Connor EF.Möck A.Waymouth RM.Hedrick JL. J. Am. Chem. Soc. 2003, 125: 3046 - 6c
Raynaud J.Ciolino A.Baceiredo A.Destarac M.Bonnette F.Kato T.Gnanou Y.Taton D. Angew. Chem. Int. Ed. 2008, 47: 5390 - 6d
Raynaud J.Ottou WN.Gnanou Y.Taton D. Chem. Commun. 2009, 6249 - 7a
Zhang YR.He L.Wu X.Shao PL.Ye S. Org. Lett. 2008, 10: 277 - 7b
Duguet N.Campbell CD.Slawin AMZ.Smith AD. Org. Biomol. Chem. 2008, 6: 1108 - 7c
He L.Lv H.Zhang Y.-R.Ye S. J. Org. Chem. 2008, 73: 8101 - 7d
Zhang Y.-R.Lv H.Zhou D.Ye S. Chem. Eur. J. 2008, 14: 8473 - 7e
Huang X.-L.He L.Shao P.-L.Ye S. Angew. Chem. Int. Ed. 2009, 48: 192 - 7f
Wang X.-N.Shao P.-L.Lv H.Ye S. Org. Lett. 2009, 11: 4029 - 7g
Lv H.You L.Ye S. Adv. Synth. Catal. 2009, 351: 2822 - For selected examples, see:
- 8a
Li G.-Q.Dai L.-X.You S.-L. Org. Lett. 2009, 11: 1623 - 8b
Hirano K.Biju AT.Piel I.Glorius F. J. Am. Chem. Soc. 2009, 131: 14190 - 8c
Riduan SN.Zhang Y.Ying JY. Angew. Chem. Int. Ed. 2009, 48: 3322 - 8d
Kawanaka Y.Phillips EM.Scheidt KA. J. Am. Chem. Soc. 2009, 131: 18028 - 8e
Raveendran AE.Paul RR.Suresh E.Nair V. Org. Biomol. Chem. 2010, 4: 901 - 8f
Biju AT.Wurz NE.Glorius F. J. Am. Chem. Soc. 2010, 132: 5970 - 8g
Vora HU.Rovis T. J. Am. Chem. Soc. 2010, 132: 2860 - 8h
Sarkar S.Grimme S.Studer A. J. Am. Chem. Soc. 2010, 132: 1190 - 8i
Gu L.Zhang Y. J. Am. Chem. Soc. 2010, 132: 914 - 9
Song J.Tan Z.Reeves JT.Gallou F.Yee NK.Senanayake CH. Org. Lett. 2005, 7: 2193 - 10a
Song JJ.Gallou F.Reeves JT.Tan ZL.Yee NK.Senanayake CH. J. Org. Chem. 2006, 71: 1273 - 10b
Suzuki Y.Abu Bakar MD.Muramatsu K.Sato M. Tetrahedron 2006, 62: 4227 - 10c
Suzuki Y.Muramatsu K.Yamauchi K.Morie Y.Sato M. Tetrahedron 2006, 62: 302 - 10d
Kano T.Sasaki K.Konishi T.Mii H.Maruoka K. Tetrahedron Lett. 2006, 47: 4615 - 10e
Fukuda Y.Maeda Y.Ishii S.Kondo K.Aoyama T. Synthesis 2006, 589 - 10f
Fukuda Y.Kondo K.Aoyama T. Synthesis 2006, 2649 - 10g
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Synthesis 2006, 1937 - 10h
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Chem. Pharm. Bull. 2006, 54: 397 - 11
Song J.Tan Z.Reeves JT.Yee NK.Senanayake CH. Org. Lett. 2007, 9: 1013 - 12a
Wu J.Sun X.Xia HG. Eur. J. Org. Chem. 2005, 4769 - 12b
Wu J.Sun XY.Ye SQ.Sun W. Tetrahedron Lett. 2006, 47: 4813 - 12c
Sun X.Ye S.Wu J. Eur. J. Org. Chem. 2006, 4787 - 12d
Liu YK.Li R.Yue L.Li BJ.Chen YC.Wu Y.Ding LS. Org. Lett. 2006, 8: 1521 - 13
Du G.-F.He L.Gu C.-Z.Dai B. Synlett 2010, 2513 - For reviews, see:
- 14a
Gröger H.Hammer B. Chem. Eur. J. 2000, 6: 943 - 14b
Kolodiazhnyi OI. Tetrahedron: Asymmetry 2005, 16: 3295 - 14c
Kolodiazhnyi OI. Russ. Chem. Bull. 2006, 75: 227 - 15a
Atherton FR.Hassall CH.Lambert RW. J. Med. Chem. 1986, 29: 29 - 15b
Hammerschmidt F. Angew. Chem. Int. Ed. Engl. 1994, 33: 341 ; Angew. Chem. 1994, 106, 334 - 16a
Jennings LJ.Macchia M.Parkin A. J. Chem. Soc., Perkin Trans. 1 1992, 2197 - 16b
Huang J.Chen R. Heteroat. Chem. 2000, 11: 480 - 17
Lavielle G.Hautefaye P.Schaeffer C.Boutin JA.Cudennec CA.Pierré A. J. Med. Chem. 1991, 34: 1998 - 18a
Natchev IA. Liebigs Ann. Chem. 1988, 861 - 18b
Mao MK.Franz JE. Synthesis 1991, 920 - 19
Emsley J.Hall D. The Chemistry of Phosphorus Harper and Row; London: 1976. p.494 - For reviews, see:
- 20a
Merino P.López EM.Herrera RP. Adv. Synth. Catal. 2008, 350: 1195 - 20b
Ma J.-A. Chem. Soc. Rev. 2006, 35: 630 - 20c
Kolodiazhnyi OI. Tetrahedron: Asymmetry 1998, 9: 1279 - 20d
Pudovik AN.Konovalova IV. Synthesis 1979, 81 - For recent examples of hydrophosphonylation reactions, see:
- 20e
Suyama K.Sakai Y.Matsumoto K.Saito B.Katsuki T. Angew. Chem. Int. Ed. 2010, 49: 797 - 20f
Nakamura S.Hayashi M.Hiramatsu Y.Shibata N.Funahashi Y.Toru T.
J. Am. Chem. Soc. 2009, 131: 18240 - 20g
Uraguchi D.Ito T.Ooi T. J. Am. Chem. Soc. 2009, 131: 3836 - 20h
Zhou X.Liu Y.Chang L.Zhao J.Shang D.Liu X.Lin L.Feng X.-M. Adv. Synth. Catal. 2009, 351: 2567 - 20i
Akiyama T.Morita H.Bachu P.Mori K.Yamanaka M.Hirata T. Tetrahedron 2009, 65: 4950 - 20j
Noronha RG.Costa PJ.Romaõ CC.Fernandes AC. Organometallics 2009, 28: 6206 - 20k
Wang F.Liu X.-H.Cui X.Xiong Y.Zhou X.Feng X.-M. Chem. Eur. J. 2009, 15: 589 - 20l
Zhou X.Liu XH.Yang X.Shang DJ.Xin JG.Feng X.-M. Angew. Chem. Int. Ed. 2008, 47: 392 - 20m
Yang F.Zhao DB.Lan JB.Xi PH.Yang L.Xiang SH.You J. Angew. Chem. Int. Ed. 2008, 47: 5646 - 20n
Tajbakhsh M.Heydari A.Khalilzadeh M.-A.Lakouraj M.-M.Zamenian B.Khaksar S. Synlett 2007, 2347 - 21a
Hatano M.Suzuki S.Takagi E.Ishihara K. Tetrahedron Lett. 2009, 50: 3171 - 21b
Das B.Balasubramanyam P.Krishnaiah M.Veeranjaneyulu B.Reddy GC. J. Org. Chem. 2009, 74: 4393 - 22
Arduengo AJ.Krafczyk R.Schmutzler R. Tetrahedron 1999, 55: 14523 - 23
Ghadwal RS.Sen SS.Roesky HW.Tavcar G.Merkel S.Stalke D. Organometallics 2009, 28: 6347 - 24
Kerr MS.de Alaniz JR.Rovis T. J. Org. Chem. 2005, 70: 5725 - 25a
Jacques J.Leclercq M.Brienne M.-J. Tetrahedron 1981, 37: 1727 - 25b
Devitt P.-G.Mitchell M.-C.Weetman J.-M.Taylor R.-J.Kee T.-P. Tetrahedron: Asymmetry 1995, 6: 2039 - 25c
Azizi N.Saidi M.-R. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178: 1255 - 25d
Elio N.Antonella R. Gazz. Chim. Ital. 1989, 119: 19