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 2004(17): 2787-2798
DOI: 10.1055/s-2004-831257
DOI: 10.1055/s-2004-831257
PAPER
© Georg Thieme Verlag Stuttgart · New YorkRhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines
Further Information
Received
19 May 2004
Publication Date:
07 October 2004 (online)
Publication History
Publication Date:
07 October 2004 (online)

Abstract
The rhodium(II)-catalyzed reaction of iodonium ylides with a variety of conjugated compounds has been examined. With α,β-unsaturated esters and α,β-unsaturated ketones, dihydrofurans were produced in moderate yields. Reactions with acrylonitriles yield oxazoles and dihydrofurans in moderate yields, whereas reactions with 1,3-butadienes result in dihydrofurans and dihydrooxepines in good yields, respectively. The mechanistic pathway for the formation of these products has been described in terms of a cyclopropane intermediate or a 1,3-dipolar cycloaddition mechanism.
Key words
iodonium ylides - rhodium(II)-catalyzed reaction - dihydrofurans - oxazoles - dihydrooxepines
- 1a
Koser GF. In The Chemistry of Functional Groups, Supplement D Wiley; New York: 1983. - 1b
Varvoglis A. In The Organic Chemistry of Polycoordinated Iodine VCH Publishers; New York: 1992. - 1c
Varvoglis A. In Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. - 2a
Moriarty RM.Kim J.Guo L. Tetrahedron Lett. 1993, 34: 4129 - 2b
Hadjiarapoglou LP.Spyroudis S.Varvoglis A. J. Am. Chem. Soc. 1985, 107: 7178 - 2c
Hadjiarapoglou LP.Schank K. Tetrahedron Lett. 1989, 30: 6673 - 2d
Hadjiarapoglou LP.Varvoglis A. Synthesis 1988, 913 - 3a
Kume M.Kubota T.Iso Y. Tetrahedron Lett. 1995, 36: 8043 - 3b
Muller P.Fernandez D. Helv. Chim. Acta 1995, 78: 947 - 4
Spyroudis S.Tarantili P. Tetrahedron 1994, 50: 11541 - 5a
Moriarty RM.May EJ.Guo L.Prakash O. Tetrahedron Lett. 1998, 39: 765 - 5b
Moriarty RM.May EJ.Prakash O. Tetrahedron Lett. 1997, 38: 4333 - 5c
Moriarty RM.Prakash O.Vaid RK.Zhao LJ. J. Am. Chem. Soc. 1989, 111: 6443 - 6a
Papadopoulou M.Spyroudis S.Varvoglis AJ. Org. Chem. 1985, 50: 1509 - 6b
Spyroudis S.Tarantili P. J. Org. Chem. 1993, 58: 4885 - 7a
Asouti A.Hadjiarapoglou LP. Tetrahedron Lett. 1998, 39: 9073 - 7b
Batsila C.Kostakis G.Hadjiarapoglou LP. Tetrahedron Lett. 2002, 43: 5997 - 8a
Lee YR.Jung YU. J. Chem. Soc., Perkin Trans. 1 2002, 1309 - 8b
Lee YR.Cho BS. Bull. Korean Chem. Soc. 2002, 23: 779 - 9a
Dean FM. In Advances in Heterocyclic Chemistry Vol. 30:Katritzky AR. Academic Press; New York: 1982. p.167-238 - 9b
Dean FM.Sargent MV. In Comprehensive Heterocyclic Chemistry Vol. 4, Part 3:Bird CW.Cheeseman GWH. Pergamon Press; New York: 1984. p.531-598 - 9c
Lipshutz BH. Chem. Rev. 1986, 86: 795 - 9d
Lee J.Li J.-H.Oya S.Snyder JK. J. Org. Chem. 1992, 57: 5301 - 9e
Jacobi PA.Selnick HG. J. Org. Chem. 1990, 55: 202 - 9f
Schabbert S.Schaumann E. Eur. J. Org. Chem. 1998, 1873 - 9g
Schuda PF. Top. Curr. Chem. 1980, 91: 75 - 9h
Zecchi G. Synthesis 1991, 181 - 9i
Ko H.-H.Yang S.-Z.Lin C.-N. Tetrahedron Lett. 2001, 42: 5269 - 9j
Bacher M.Hofer O.Brader G.Vajrodaya S.Greger H. Phytochemistry 1999, 52: 253 - 9k
Hakim EH.Fahriyati A.Kau MS.Achmad AA.Makmur L.Ghisalberti EL.Nomura T. J. Nat. Prod. 1999, 62: 613 - 9l
Reddy MVB.Reddy MK.Gunasekar D.Caux C.Bodo B. Phytochemistry 2003, 64: 879 - 9m
Diaz JG.Goedken VL.Herz W. Phytochemistry 1992, 31: 597 - 9n
Hashemi-Nejad NM.Jakupovic J.Castro V. Phytochemistry 1990, 29: 3030 - 10a
Nakanishi K. Natural Products Chemistry Academic; New York: 1974. - 10b
The Chemistry of Heterocyclic Flavoring and Aroma Compounds
Vernin G. Ellis Horwood; Chichester: 1982. - 10c
Merrit AT.Ley SV. Nat. Prod. Rep. 1992, 9: 243 - 10d
Fraga BM. Nat. Prod. Rep. 1992, 9: 217 - 10e
Kubo I.Lee YW.Balogh-Nair V.Nakanishi K.Chapya A. J. Chem. Soc., Chem. Commun. 1976, 949 - 10f
Schulte G.Scheuer PJ.McConnell OJ. Helv. Chim. Acta 1980, 63: 2159 - 10g
Inoue K.Sugaya T.Ogasa T.Tomioka S. Synthesis 1997, 113 - 10h
Sarkhel S.Sharon A.Trivedi V.Maulik PR.Singh MM.Venugopalan P.Ray S. Bioorg. Med. Chem. 2003, 11: 5025 - 11
Koser GF.Yu S.-M. J. Org. Chem. 1975, 40: 1166 - 12
Fairfax DJ.Austin DJ.Xu SL.Padwa A. J. Chem. Soc., Perkin Trans. 1 1992, 2837 - 13
Hadjiarapoglou LP.Schank K. Tetrahedron 1997, 53: 9365 - 14a
Pirrung MC.Blume F. J. Org. Chem. 1999, 64: 3642 - 14b
Pirrung MC.Lackey K.Zhang J.Sternbach DD.Brown F. J. Org. Chem. 1995, 60: 2112 - 15
Lee YR.Suk JY.Kim BS. Tetrahedron Lett. 1999, 403: 6603 - 16
West FG.Naidu BN. J. Am. Chem. Soc. 1993, 115: 1177