Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Matthew D. Hassink; Joseph M. Fox

doi:10.1055/s-0031-1290822

Synthesis, Table of Contents

Synthesis 2012; 44(18): 2843-2850
DOI: 10.1055/s-0031-1290822

special topic

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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Abstract

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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.

Key words

cyclopropene - chirality - dianions - strained ring systems - rearrangement

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References

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 S_N2′, 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

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