Synthesis 2012; 44(18): 2843-2850
DOI: 10.1055/s-0031-1290822
special topic
© Georg Thieme Verlag Stuttgart · New York

Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Matthew D. Hassink
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, eMail: jmfox@udel.edu
,
Joseph M. Fox*
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, eMail: jmfox@udel.edu
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Publikationsverlauf

Received: 29. Februar 2012

Accepted: 09. März 2012

Publikationsdatum:
08. Mai 2012 (online)


Abstract

1,2-Disubstituted 3-hydroxymethylcyclopropene derivatives have been synthesized by reacting the dianions of 1-alkyl-3-hydroxymethylcyclopropenes with a range of electrophiles. Additionally, a complementary procedure is described for one-pot sequential alkylation/rearrangement to provide a convenient synthesis of a chiral methylenecyclopropane directly from a 1-alkyl-3-hydroxymethylcyclopropene.

Supporting Information

 
  • References

    • For reviews, see:

    • 1a Miege F, Meyer C, Cossy J. Beilstein J. Org. Chem. 2011; 7: 717
    • 1b Marek I, Simaan S, Masarwa A. Angew. Chem. Int. Ed. 2007; 46: 7364
    • 1c Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
    • 1d Rubin M, Rubina M, Gevorgyan V. Synthesis 2006; 1221
    • 1e Fox JM, Yan N. Curr. Org. Chem. 2005; 9: 719
    • 1f Nakamura M, Isobe H, Nakamura E. Chem. Rev. 2003; 103: 1295
    • 1g Halton B, Banwell MG In The Chemistry of the Cyclopropyl Group . Patai S, Rappoport Z. Wiley; Chichester: 1987: 1224
    • 1h Baird MS. Top. Curr. Chem. 1988; 144: 139
    • 1i Baird MS, Schmidt T In Carbocyclic Three-Membered Ring Compounds . de Meijere A. Georg Thieme Verlag; Stuttgart: 1996: 114
    • 2a Vincens M, Dumont C, Vidal M, Domnin IN. Tetrahedron 1983; 39: 4281
    • 2b D’yakonov IA, Kostikov RR. J. Gen. Chem. USSR (Engl. Transl.) 1964; 34: 1722
    • 2c Vincens M, Fadel R, Vidal M. Bull. Soc. Chim. Fr. 1987; 3: 462
    • 3a Liao L, Fox JM. J. Am. Chem. Soc. 2002; 124: 14322
    • 3b Liu X, Fox JM. J. Am. Chem. Soc. 2006; 128: 5600
    • 3c Yan N, Liu X, Fox JM. J. Org. Chem. 2008; 73: 563
    • 3d Richey HG. Jr, Bension RM. J. Org. Chem. 1980; 45: 5036
    • 3e For carbomagnesation reactions that are directed by allylic hydroxyl substituents, see: Simaan S, Marek I. Org. Lett. 2007; 9: 2569
    • 4a Yang Z, Xie X, Fox JM. Angew. Chem. Int. Ed. 2006; 45: 3960
    • 4b Xie X, Yang Z, Fox JM. J. Org. Chem. 2010; 75: 3847

    • For related work with allylic hydroxy substitutents, see:
    • 4c Masarwa A, Stanger A, Marek I. Angew. Chem. Int. Ed. 2007; 46: 8039
    • 4d Simaan S, Masarwa A, Bertus P, Marek I. Angew. Chem. Int. Ed. 2006; 45: 3963
    • 5a Phan DH. T, Kou KG. M, Dong VM. J. Am. Chem. Soc. 2010; 132: 16354
    • 5b Bugaut X, Liu F, Glorius F. J. Am. Chem. Soc. 2011; 133: 8130
  • 6 Miege F, Meyer C, Cossy J. Org. Lett. 2010; 12: 248
  • 7 Rubina M, Woodward EW, Rubin M. Org. Lett. 2007; 9: 5501
    • Additional reactions of 3-hydroxymethylcyclopropenes include:

    • 8a Allylindanation reactions: Araki S, Kenji O, Shiraki F, Hirashita T. Tetrahedron Lett. 2002; 43: 8033
    • 8b Carbozincation reactions: Kramer K, Leong P, Lautens M. Org. Lett. 2011; 13: 819
    • 9a Doyle MP, Protopova M, Müller P, Ene D, Shapiro EA. J. Am. Chem. Soc. 1994; 116: 8492
    • 9b Davies HM. L, Lee GH. Org. Lett. 2004; 6: 1233
    • 9c Briones J, Hansen J, Hardcastle K, Autschbach J, Davies HM. L. J. Am. Chem. Soc. 2010; 132: 17211
    • 9d Lou Y, Horikawa M, Kloster R, Hawryluk N, Corey EJ. J. Am. Chem. Soc. 2004; 126: 8916
    • 9e Goto T, Takeda K, Shimada N, Nambu H, Anada M, Shiro M, Ando K, Hashimoto S. Angew. Chem. Int. Ed. 2011; 50: 6803
    • 9f Boruta DT, Dmitrenko O, Yap GP. A, Fox JM. Chem. Sci. 2012; 3: 1589
    • 10a Pallerla MK, Fox JM. Org. Lett. 2007; 9: 5625
    • 10b Pallerla MK, Fox JM. Org. Lett. 2005; 7: 3593
    • 10c Pallerla MK, Yap GP. A, Fox JM. J. Org. Chem. 2008; 73: 6137
    • 10d Kireev SL, Smit VA, Ugrak BI, Nefedov OM. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1991; 40: 2240
    • 11a Closs GL, Closs LE. J. Am. Chem. Soc. 1963; 85: 99
    • 11b Avezov IB, Bolesov IG, Levina RY. J. Org. Chem. USSR, Div. Chem. Sci. (Engl. Trans.) 1974; 10: 2129
    • 11c Isaka M, Matsuzawa S, Yamago S, Ejiri S, Miyachi Y, Nakamura E. J. Org. Chem. 1989; 54: 4727
    • 11d Kirms MA, Primke H, Stohlmeier M, de Meijere A. Recl. Trav. Chim. Pays-Bas 1986; 105: 462
    • 11e Schipperijn AJ, Smael P. Recl. Trav. Chim. Pays-Bas 1973; 92: 1159
    • 12a Zrinski I, Novak-Coumbassa N, Eckert-Maksic M. Organometallics 2004; 23: 2806
    • 12b Zrinski I, Eckert-Maksić M. Synth. Commun. 2003; 33: 4071
    • 13a Liao L, Yan N, Fox JM. Org. Lett. 2004; 6: 4937
    • 13b Fisher LA, Fox JM. J. Org. Chem. 2008; 73: 8474
  • 14 Chuprakov S, Rubin M, Gevorgyan V. J. Am. Chem. Soc. 2005; 127: 3714
  • 15 Fordyce EA. F, Luebbers T, Lam HW. Org. Lett. 2008; 10: 3993
  • 16 Kim R, Sherrill WM, Rubin M. Tetrahedron 2010; 66: 4947
  • 17 Audran G, Pellissier H. Adv. Synth. Catal. 2010; 352: 575
    • Formal SN2′, see:

    • 18a Nueske H, Bräse S, Meijere A. Synlett 2000; 1467
    • 18b Babin D, Pilorge F, Delbarre LM, Demoute JP. Tetrahedron 1995; 51: 9603
    • 18c Ref. 4d
    • 18d Weatherhead-Kloster RA, Corey EJ. Org. Lett. 2006; 8: 171

    • Reduction with allylic transposition, see:
    • 18e Simaan S, Marek I. Chem. Commun. 2009; 3: 292
    • 18f Simaan S, Masarwa A, Zohar E, Stanger A, Marek I, Bertus P. Chem.–Eur. J. 2009; 15: 8449

    • For allylic chlorination, see:
    • 18g Arnaud R, Choubani S, Subra R, Vidal M, Vincens M. Can. J. Chem. 1985; 63: 2512
    • 18h Vincens M, Choubani S, Vidal M. Tetrahedron Lett. 1981; 22: 4695

    • For sigmatropic rearrangement, see:
    • 18i Ref. 7
    • 18j Ref. 4c
    • 18k Ref. 18f
    • 19a Yamago S, Nakamura M, Wang X, Yanagawa M, Tokumitsu S, Nakamura E. J. Org. Chem. 1998; 63: 1694
    • 19b Yamago S, Nakamura E. J. Am. Chem. Soc. 1989; 111: 7285
    • 19c Vincens M, Dumont C, Vidal M. Tetrahedron 1981; 37: 2683
    • 19d Audo D, Vincens M, Dumont C, Vidal M. Can. J. Chem. 1981; 59: 2199
    • 19e Vidal M, Vincens M, Arnaud P. Bull. Soc. Chim. Fr. 1972; 2: 665
    • 19f Padwa A, Wannamaker W. Tetrahedron 1991; 32: 6139
    • 19g Okazaki R, O-oka M, Akiyama T, Inamoto N, Niwa J, Kato S. J. Am. Chem. Soc. 1987; 109: 5413
    • 19h Stierman TJ, Johnson RP. J. Am. Chem. Soc. 1983; 105: 2492
    • 19i Formanovskii AA, Leonova LI, Yakushkina NI, Bakhbukh M, Grishin YuK, Bolesov IG. Zh. Org. Khim. 1977; 13: 1883
    • 19j Nakamura M, Toganoh M, Wang X, Yamago S, Nakamura E. Chem. Lett. 2000; 6: 664
    • 19k Vincens M, Vidal M. Bull. Soc. Chim. Fr. 1985; 5: 900
    • 19l Richey H, Wilkins C, Bension R. J. Org. Chem. 1980; 45: 5042
    • 19m Warkentin J, Woollard J. Can. J. Chem. 1997; 75: 289
    • 19n Vincens M, Dumont C, Vidal M. Bull. Soc. Chim. Fr. 1974; 2811
  • 20 Jackman LM, Smith BD. J. Am. Chem. Soc. 1988; 110: 3829