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Synthesis 2011(12): 1984-1987
DOI: 10.1055/s-0030-1260052
DOI: 10.1055/s-0030-1260052
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkDiastereoselective Synthesis of Bicyclo[2.2.2]octan-2-one Derivatives through an Unexpected Organocatalytic Tandem Michael-Michael Reaction
Weitere Informationen
Received
11 April 2011
Publikationsdatum:
17. Mai 2011 (online)
Publikationsverlauf
Publikationsdatum:
17. Mai 2011 (online)
Abstract
An organocatalytic tandem Michael-Michael reaction is developed for the simple preparation of stereo complex, polycyclic compounds from simple reactants in satisfactory yields (up to 90%) and excellent diastereoselectivities (>30:1 dr).
Key words
organocatalysis - Michael reaction - tandem reaction - α,β-unsaturated ketones
- Supporting Information for this article is available online:
- Supporting Information
- For selected examples, see:
- 1a
Jauch J. Eur. J. Org. Chem. 2001, 66: 473 - 1b
Movassaghi M.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 2456 - 1c
He Y.-T.Yang H.-N.Yao Z.-J. Tetrahedron 2002, 58: 8805 - 1d
Grossmann G.Poncioni M.Bornand M.Jolivet B.Neuburger M.Séquin U. Tetrahedron 2003, 59: 3237 - 1e
Adrio J.Carretero JC. J. Am. Chem. Soc. 2007, 129: 778 - 1f
Patil SN.Liu F. J. Org. Chem. 2008, 73: 4476 - 1g
Casiraghi G.Zanardi F.Battistini L.Rassu G. Synlett 2009, 1525 - 1h
Kitajima H.Ito K.Katsuki T. Tetrahedron 1997, 53: 17015 - 1i
Kitajima H.Ito K.Katsuki T. Synlett 1997, 568 - 1j
Nishikori H.Ito K.Katsuki T. Tetrahedron: Asymmetry 1998, 9: 1165 - 1k
Desimoni G.Faita G.Filippone S.Mella M.Zamponi MG.Zema M. Tetrahedron 2001, 57: 10203 - 1l
Kim JN.Lee HJ.Gong JH. Tetrahedron Lett. 2002, 43: 9141 - 1m
Cho C.-W.Kong J.-R.Krische MJ. Org. Lett. 2004, 6: 1337 - 1n
Du Y.Han X.Lu X. Tetrahedron Lett. 2004, 45: 4967 - 1o
Park H.Cho C.-W.Krische MJ. J. Org. Chem. 2006, 71: 7892 - 1p
Suga H.Takemoto H.Kakehi A. Heterocycles 2007, 71: 361 - 1q
Zhang T.-Z.Dai L.-X.Hou X.-L. Tetrahedron: Asymmetry 2007, 18: 1990 - 1r
van Steenis DJVC.Marcelli T.Lutz M.Spek AL.van Maarseveen JH.Hiemstra H. Adv. Synth. Catal. 2007, 349: 281 - 1s
Yang H.Kim S. Synlett 2008, 555 - 1t
Ma G.-N.Cao S.-H.Shi M. Tetrahedron: Asymmetry 2009, 20: 1086 - 1u
Hyde AM.Buchwald SL. Org. Lett. 2009, 11: 2663 - For reviews on the synthesis of butenolides, see:
- 2a
Rao YS. Chem. Rev. 1964, 64: 353 - 2b
Negishi E.Kotora M. Tetrahedron 1997, 53: 6707 - 2c
Montagnon T.Tofi M.Vassilikogiannakis G. Acc. Chem. Res. 2008, 41: 1001 - For examples of natural products containing the butenolide unit, see:
- 3a
Carmen Zafra-Polo M.Figadère B.Gallardo T.Tormo JR.Cortes D. Phytochemistry 1998, 48: 1087 - 3b
Alali FW.Liu X.-X.McLaughlin JL.
J. Nat. Prod. 1999, 62: 504 - 3c
de March P.Figueredo M.Font J.Raya J.Alvarez-Larena A.Piniella JF. J. Org. Chem. 2003, 68: 2437 - 3d
Yoshimitsu T.Makino T.Nagaoka H. J. Org. Chem. 2004, 69: 1993 - 3e
Gao S.Wang Q.Chen C. J. Am. Chem. Soc. 2009, 131: 1410 - Selected recent examples of reactions with 2-silyloxyfurans: Mannich:
- 4a
Carswell EL.Snapper ML.Hoveyda AH. Angew. Chem. Int. Ed. 2006, 45: 7230 - 4b
Yamaguchi A.Matsunaga S.Shibasaki M. Org. Lett. 2008, 10: 2319 - 4c
González AS.Arrayás RG.Rivero MR.Carretero JC. Org. Lett. 2008, 10: 4335 - 4d
Mandai H.Mandai K.Snapper ML.Hoveyda AH. J. Am. Chem. Soc. 2008, 130: 17961 - 4e
Jiang Y.-Q.Shi Y.-L.Shi M. J. Am. Chem. Soc. 2008, 130: 7202 - 4f
Akiyama T.Honma Y.Itoh J.Fuchibe K. Adv. Synth. Catal. 2008, 350: 399 - 4g
Wieland LC.Vieira EM.Snapper ML.Hoveyda AH. J. Am. Chem. Soc. 2009, 131: 570 - Aldol:
- 4h
Das Sarma K.Zhang J.Curran TT. J. Org. Chem. 2007, 72: 3311 - 4i
Fabra MJ.Fraile JM.Herrerías CI.Lahoz FJ.Mayoral JA.Pérez I. Chem. Commun. 2008, 5402 - 4j
Frings M.Atodiresei I.Runsink J.Raabe G.Bolm C. Chem. Eur. J. 2009, 15: 1566 - 4k
Singh RP.Foxman BM.Deng L. J. Am. Chem. Soc. 2010, 132: 9558 - Michael:
- 4l
Okano T.Eguchi S.Hayakawa Y. Tetrahedron 2000, 56: 6219 - 4m
Desimoni G.Faita G.Filippone S.Mella M.Zampori MG.Zema M. Tetrahedron 2001, 57: 10203 - 4n
Brown SP.Goodwin NC.MacMillan DWC. J. Am. Chem. Soc. 2003, 125: 1192 - 4o
Huang Y.Walji AM.Larsen CH.MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051 - 4p
Yadav JS.Reddy BVS.Narasimhulu G.Reddy NS.Reddy PG. Tetrahedron Lett. 2008, 49: 5683 - For recent examples with 2(5H)-furanone and related compounds as direct nucleophiles, see:
- 5a
Yamaguchi A.Matsunaga S.Shibasaki M. Org. Lett. 2008, 10: 2319 - 5b
Trost BM.Hitce J. J. Am. Chem. Soc. 2009, 131: 4572 - 5c
Hyde AM.Buchwald SL. Org. Lett. 2009, 11: 2663 - 5d
Shepherd NE.Tanabe H.Xu Y.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2010, 132: 3666 - 5e
Huang J.-R.Lei J.Wang Z.-F.Chen S.Wu L.Chen Y.-C. Org. Lett. 2010, 12: 720 - 5f
Wang J.Qi C.Ge Z.Cheng T.Li R. Chem. Commun. 2010, 46: 2124 - 5g
Zhang Y.Yu C.Ji Y.Wang W. Chem. Asian J. 2010, 5: 1303 - 5h
Yang Y.Zheng K.Zhao J.Shi J.Liu X.Feng X. J. Org. Chem. 2010, 75: 5382 - 5i
Ube H.Shimada N.Terada M. Angew. Chem. Int. Ed. 2010, 49: 1858 - 6a
Huang H.Yu F.Jin Z.Li W.Wu W.Liang X.Ye J. Chem. Commun. 2010, 46: 5957 - 6b
Huang H.Jin Z.Zhu K.Liang X.Ye J. Angew. Chem. Int. Ed. 2011, 50: 3232 - 7
Zhang Y.Shao Y.-L.Xu H.-S.Wang W. J. Org. Chem. 2011, 76: 1472 - For selected recent examples of primary amine catalyzed reactions, see:
- 8a
Huang H.Jacobsen EN. J. Am. Chem. Soc. 2006, 128: 7170 - 8b
Lalonde MP.Chen Y.Jacobsen EN. Angew. Chem. 2006, 118: 6514 - 8c
Wang X.Reisinger CM.List B. J. Am. Chem. Soc. 2008, 130: 6070 - 8d
Singh RP.Bartelson K.Wang Y.Su H.Lu X.Deng L. J. Am. Chem. Soc. 2008, 130: 2422 - 8e
Xu L.-W.Lu Y.-X. Chem. Commun. 2009, 1807 - For recent reports of bifunctional primary amine-thiourea mediated catalysis, see:
- 8f
Xu Y.Córdova A. Chem. Commun. 2006, 460 - 8g
Zhang X.Liu S.Li X.Yan M.Chan ASC. Chem. Commun. 2009, 833 - For direct vinylogous reactions of α,β-unsaturated γ-butyrolactam and related donors, see:
- 9a
Sartori A.Curti C.Battistini L.Burreddu P.Rassu G.Pelosi G.Casiraghi G.Zanardi F. Tetrahedron 2008, 64: 11697 - 9b
Curti C.Sartori A.Battistini L.Rassu G.Burreddu P.Zanardi F.Casiraghi G. J. Org. Chem. 2008, 73: 5446 - 9c
Shepherd NE.Tanabe H.Xu Y.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2010, 132: 3666 - 9d
Feng X.Cui H.-C.Shi X.Wu L.Chen Y.-C. Chem. Eur. J. 2010, 16: 10309 - 11a
Li P.Wang Y.Liang X.Ye J. Chem. Commun. 2008, 3302 - 11b
Li P.Wen S.Yu F.Liu Q.Li W.Wang Y.Liang X.Ye J. Org. Lett. 2009, 11: 753 - 11c
Wen S.Li P.Wu H.Yu F.Liang X.Ye J. Chem. Commun. 2010, 46: 4806 - 11d
Zhou Y.Li X.Li W.Wu W.Liang X.Ye J. Synlett 2010, 2357 - 11e
Yu F.Jin Z.Huang H.Ye T.Liang X.Ye J. Org. Biomol. Chem. 2010, 8: 4767 - 11f
Yu F.Sun X.Jin Z.Wen S.Liang X.Ye J. Chem. Commun. 2010, 46: 4589 - 11g
Yang J.Li W.Jin Z.Liang X.Ye J. Org. Lett. 2010, 12: 5218
References
The crystallographic data for structure 3h in this paper have been deposited at the Cambridge Crystallographic Data Centre, Cambridge, CB2 1EZ, United Kingdom (CCDC 804550).