Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(4): 609-614
DOI: 10.1055/s-2006-926298
DOI: 10.1055/s-2006-926298
PAPER
© Georg Thieme Verlag Stuttgart · New YorkCeric(IV)-Mediated Reaction of Methylenecyclopropanes in Organic Synthesis: A Facile Access to Dihydrofurans and Cyclobutanones
Further Information
Received
13 July 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
Abstract
Alkylidenecyclopropanes undergo CAN-mediated addition reactions with 1,3-dicarbonyl compounds or ring rearrangement reactions leading to dihydrofuran and cyclobutanone derivatives, respectively, in moderate yields.
Key words
methylenecyclopropanes - ammonium cerium(IV) nitrate - 1,3-dicarbonyl compounds - dihydrofuran - cyclobutanone
- 1a
Brandi A.Goti A. Chem. Rev. 1998, 98: 589 - 1b
Brandi A.Cicchi S.Cordero FM.Goti A. Chem. Rev. 2003, 103: 1213 - 1c
Yamago S.Nakamura E. Org. React. 2002, 61: 1 - 1d
Nakamura E.Yamago S. Acc. Chem. Res. 2002, 35: 867 - 1e
Yamago S.Takeichi A.Nakamura E. Synthesis 1996, 1380 - 2a
Binger P.Büch H.M . Top. Curr. Chem. 1987, 135: 77 - 2b
Ohta T.Takaya H. In Comprehensive Organic Synthesis Vol. 5:Trost BM. Pergamon; Oxford: 1991. p.1185 - 2c
Suginome M.Matsuda T.Ito Y. J. Am. Chem. Soc. 2000, 122: 11015 - 2d
Nakamura I.Saito S.Yamamoto Y. J. Am. Chem. Soc. 2000, 122: 2661 - 2e
Oh BH.Nakamura I.Saito S.Yamamoto Y. Tetrahedron Lett. 2001, 42: 6203 - 2f
Camacho DH.Nakamura I.Saito S.Yamamoto Y. J. Org. Chem. 2001, 66: 270 - 2g
Nakamura I.Oh BH.Saito S.Yamamoto Y. Angew. Chem. Int. Ed. 2001, 40: 1298 - 2h
Nakamura I.Siriwardana AI.Saito S.Yamamoto Y. J. Org. Chem. 2002, 67: 3445 - 2i
Camacho DH.Nakamura I.Oh BH.Saito S.Yamamoto Y. Tetrahedron Lett. 2002, 43: 2903 - 2j
Siriwardana AI.Nakamura I.Yamamoto Y. Tetrahedron Lett. 2003, 44: 985 - 2k
Xu B.Shi M. Org. Lett. 2003, 5: 1415 - 2l
Ma S.Lu L.Zhang J. J. Am. Chem. Soc. 2004, 126: 9645 - 2m
López F.Delgado A.Rodriguez JR.Castedo L.Mascareñas JL. J. Am. Chem. Soc. 2004, 126: 10262 - 2n
Nötzel MW.Tamm M.Labahn T.Noltemeyer M.Es-Sayed M.de Meijere A. J. Org. Chem. 2000, 65: 3850 - 2o
Nötzel MW.Labahn T.Es-Sayed M.de Meijere A. Eur. J. Org. Chem. 2001, 3025 - 2p
Nakamura I.Yamamoto Y. Adv. Synth. Catal. 2002, 344: 111 - 3a
Melikyan GG. Org. React. 1997, 49: 427 - 3b
Snider BB. Chem. Rev. 1996, 96: 339 - 3c
Linker T. J. Organomet. Chem. 2002, 661: 159 - 3d
Nair V.Mathew J.Prabhakaran J. Chem. Soc. Rev. 1997, 127 - 3e
Vinogradov MG.Kondorsky AE.Nikishin GI. Synthesis 1988, 60 - 3f
Lee YR.Suk JY.Kim BS. Org. Lett. 2000, 2: 1387 - 3g
Hong BC.Shen IC.Liao JH. Tetrahedron Lett. 2001, 42: 935 - 4a
Nair V.Balagopal L.Rajan R.Mathew J. Acc. Chem. Res. 2004, 37: 21 - 4b
Nair V.Mathew J.Radhakrishnan KV. J. Chem. Soc., Perkin Trans. 1 1996, 1487 - 4c
Kajikawa S.Nishino H.Kurosawa K. Heterocycles 2001, 54: 171 - 4d
Lee YR.Kim BS.Kim DH. Tetrahedron 2000, 56: 8845 - 4e
Miura M.Arai N.Narasaka K. Bull. Chem. Soc. Jpn. 1998, 71: 1437 - 4f
Lee YR.Byun MW.Kim BS. Bull. Korean Chem. Soc. 1998, 19: 1080 - 4g
Nair V.Mathew J.Kanakamma PP.Panicker SB.Sheeba V.Zeena S.Eigendorf GK. Tetrahedron Lett. 1997, 38: 2191 - 4h
Nair V.Sheeba V.Panicker SB.George TG.Rajan R.Balagopal L.Vairamani M.Prabhakar S. Tetrahedron 2000, 56: 2461 - For radical reactions related to MCPs, see:
- 5a
Mizuno K.Nire K.Sugita H.Otsuji Y. Tetrahedron Lett. 1993, 34: 6563 - 5b
Mizuno K.Maeda H.Sugita H.Nishioka S.Hirai T.Sugimoto A. Org. Lett. 2001, 3: 581 - 5c
Legrand N.Quiclet-Sire B.Zard SZ. Tetrahedron Lett. 2000, 41: 9815 - 5d
Destabel C.Kilburn JD.Knight J. Tetrahedron 1994, 50: 11267 - 5e
Boffey RJ.Santagostino M.Whittingham WG.Kilburn JD. Chem. Commun. 1998, 1875 - 5f
Pike KG.Destabel C.Anson M.Kilburn JD. Tetrahedron Lett. 1998, 39: 5877 - 5g
Boffey RJ.Whittingham WG.Kilburn JD. J. Chem. Soc., Perkin Trans. 1 2001, 487 - 5h
Kozhushkov SI.Brandl M.de Meijere A. Eur. J. Org.Chem. 1998, 1535 - 5i
Xu B.Chen Y.Shi M. Tetrahedron Lett. 2002, 43: 2781 - 5j
de Lijser HJP.Cameron TS.Arnold DR. Can. J. Chem. 1997, 75: 1795 - For some of the most recent results from this group, see:
- 6a
Huang X.Chen WL.Zhou HW. Synlett 2004, 329 - 6b
Huang X.Zhou H.Chen W. J. Org. Chem. 2004, 69: 839 - 6c
Chen W.Huang X.Zhou H. Synthesis 2004, 1573 - 6d
Zhou H.Huang X.Chen W. J. Org. Chem. 2004, 69: 5471 - The cyclopropylmethyl radical is stabilized by the substituents on MCP, which does not undergo a cyclopropyl ring-opening radical rearrangement. It is further oxidized by a second equivalent of CAN to give the more stable cyclopropylcarbinyl cation, see:
- 9a
Bowry VW.Lusztyk J.Ingold KU. Chem. Commun. 1990, 92 - In addition some 3-exo-trig processes have been described recently:
- 9b
Sakuma D.Togo H. Synlett 2004, 2501 - 9c
David H.Afonso C.Bonin M.Doisneau G.Guillerez M.-G.Guibé F. Tetrahedron Lett. 1999, 40: 8557 - 9d
Gansauer A.Lauterbach T.Gimbel-Geich D. Chem. Eur. J. 2004, 10: 4983 - For a stable cyclopropylcarbinyl cation, see:
- 10a
Klunder AJH.Zwanenburg B. In Houben-Weyl, Methoden der organischen Chemie Vol. E17c:de Meijere A. Thieme; Stuttgart: 1977. p.2419 - 10b
March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. p.169 ; and references cited therein - Shi has reported the ring-expansion of MCPs in the presence of DIAD or DEAD and Lewis acids in wet CH3CN, see:
- 11a
Shao LX.Shi M. Eur. J. Org. Chem. 2004, 426 - 11b de Meijere has previously reported cycloadditions onto a unique olefin bicyclopropylidene
in which the cyclobutanone was formed in the reaction between bicyclopropylidene and
4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in wet acetone, see:
de Meijere A.Erden I.Weber W.Kaufmann D. J. Org. Chem. 1988, 53: 152 - 13
Trahanovsky WS.Young LB.Brown GL. J. Org. Chem. 1967, 32: 3865 - 14
Miyashi T.Roth HD.Schilling MLM.Takahashi Y.Mukai T. J. Am. Chem. Soc. 1985, 107: 1079 - 15 During the preparation of our manuscript, manganese(III)-mediated oxidative annulation
of MCPs with 1,3-dicarbonyl compounds was reported, see:
Huang JW.Shi M. J. Org. Chem. 2005, 70: 3859 - Such cyclobutanones can be formed in the reactions between MCPs and peracetic acid or MCPBA.
- 16a
Crandall JK.Conover WW. J. Org. Chem. 1978, 43: 3533 - 16b
Aue DH.Meshishnek MJ.Shellhamer DF. Tetrahedron Lett. 1973, 14: 4799 ; and reference 3 therein - 16c
Salaün JR.Conia JM. J. Chem. Soc., Chem. Commun. 1971, 1579 - For some more papers related to the formation of cyclobutanones, see:
- 16d
Trost BM.Preckel M.Leichter LM. J. Am. Chem. Soc. 1975, 97: 2224 - 16e
Frank D.Kozhushkov SI.Labahn T.de Meijere A. Tetrahedron 2002, 58: 7001 - 16f
Trost BM. Top. Curr. Chem. 1986, 133: 3 - 16g
Nemoto H.Miyata J.Hakamata H.Nagamochi M.Fukumoto K. Tetrahedron 1995, 51: 5511 - 16h
Nemoto H.Fukumoto K. Synlett 1997, 863 - 16i
Bernard AM.Floris C.Frongia A.Piras PP. Synlett 1998, 668 - 16j
Trost BM. Acc. Chem. Res. 1974, 7: 85 - 16k Review:
Salaün JR. In The Chemistry of the Cyclopropyl GroupRappoport Z. Wiley; New York: 1987. p.809 - 16l
de Meijere A.Erden I.Weber W.Kaufmann D. J. Org. Chem. 1988, 53: 152 - 17 Substituted MCPs 1 are readily available by the reaction of aldehydes/ketones with 3-bromopropylphosphonium
bromide. It should be noted that the aryl-substituted MCPs are stable at -15 °C. For
the synthesis of MCPs, see:
Utimoto K.Tamura M.Sisido K. Tetrahedron 1973, 29: 1169
References
X-ray crystal data for compound 3a: C22H20O2, MW = 316.38, Monoclinic, space group P21/n, a = 9.9482 (12), b = 12.0846 (14), c = 13.6979 (16) Å, α = 90, β = 99.745 (2), γ = 90, V = 1623.0(3) Å3, T = 293 (2) K, Z = 4, ρcalcd = 1.295 Mg/m3, µ = 0.081 mm-1, λ = 0.71073 Å, F(000) 672.00, independent reflections (R int = 0.0794), 9396 reflections collected; refinement method, full-matrix least-squares refinement on F2; Goodness-of-fit on F2 = 0.907; Final R indices [I > 2σ(I)] R1 = 0.0470, wR2 = 0.0913.
8MCPs 1 are not very soluble in CH3CN, therefore the co-solvent THF is required.
12Due to the poor solubility of MCPs in H2O, we added THF as the co-solvent (THF-H2O, 4:1).