Iodoaminations of Alkenes

Abstract

The activation of alkenes and their subsequent functionalization is a frequently used methodology in synthetic chemistry. This review highlights recent iodine-mediated aminations and elaborates on the various strategies to bring about regio- or stereoselective transformations.

1 Introduction

2 Strategies and Mechanisms

3 N-Functionalization of Alkenes

4 Enantioselective Iodoaminations

5 Conclusions and Outlook

Key words

asymmetric synthesis - aziridines - iodoaminations - lactams - regioselectivity

• References

• 1 Bougault MJ. R. C. R. Hebd. Seances Acad. Sci. 1904; 139: 864
• 2a Qiu J, Silverman RB. J. Med. Chem. 2000; 43: 706
• 2b Pors K, Shnyder SD, Teesdale-Spittle PH, Hartley JA, Zloh M, Searcey M, Patterson LH. J. Med. Chem. 2006; 49: 7013
• 2c Kuang Y, Balakrishnan K, Gandhi V, Peng X. J. Am. Chem. Soc. 2011; 133: 19278

Selected reviews:
• 3a French AN, Bissmire S, Wirth T. Chem. Soc. Rev. 2004; 33: 354
• 3b Chen G, Ma S. Angew. Chem. 2010; 122: 8484 ; Angew. Chem. Int. Ed. 2010, 49, 8306
• 3c Castellanos Fletcher AS. P. Chem. Eur. J. 2011; 17: 5766
• 3d Tan CK, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
• 4a Hennecke U. Chem. Asian J. 2012; 7: 456
• 4b Haas J, Piguel S, Wirth T. Org. Lett. 2002; 4: 297
• 4c Haas J, Bissmire S, Wirth T. Chem. Eur. J. 2005; 11: 5777

For reviews of halocyclizations, see:
• 5a Bartlett PA In Asymmetric Synthesis . Vol. 3. Morrison JD. Academic Press; Orlando: 1984: 411
• 5b Cardillo G, Orena M. Tetrahedron 1990; 46: 3321
• 5c Harding KE, Tiner TH. Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon; New York: 1991: 363
• 6a Schmid GH, Garratt DG. The Chemistry of Double-Bonded Functional Groups . Part 2; Patai S. Wiley; New York: 1977: 725
• 6b Schmid GH. The Chemistry of Double-Bonded Functional Groups . Part 1, Vol. 2; Patai S. Wiley; New York: 1989: 679
• 7a Harding KE, Marman TH, Nam D. Tetrahedron 1988; 44: 5605
• 7b Zefirov NS. Tetrahedron 1977; 33: 2719
• 7c Rychnowsky SD, Bartlett PA. J. Am. Chem. Soc. 1981; 103: 3963
• 8a Olah GA, Bollinger JM. J. Am. Chem. Soc. 1967; 89: 4744
• 8b Olah GA, Bollinger JM. J. Am. Chem. Soc. 1968; 90: 947
• 8c Olah GA, Bollinger JM, Brinich J. J. Am. Chem. Soc. 1968; 90: 2587
• 9a Brown RS, Nagorski RW, Bennet AJ, McClung RE. D, Aarts GH. M, Klobukowski M, McDonald R, Santarsiero BD. J. Am. Chem. Soc. 1994; 116: 2448
• 9b Neverov AA, Brown RS. J. Org. Chem. 1996; 61: 962
• 9c Brown RS. Acc. Chem. Res. 1997; 30: 131
• 9d Denmark SE, Kuester WE, Burk MT. Angew. Chem. 2012; 124: 11098 ; Angew. Chem. Int. Ed. 2012, 51, 10938
• 10 Cardillo G, Orena M, Porzi G, Sandri S. J. Chem. Soc., Chem. Commun. 1982; 1308
• 11 Bongini A, Cardillo G, Orena M, Sandri S, Tomasini C. J. Org. Chem. 1986; 51: 4905
• 12 Knapp S, Sankar Lal G, Sahai D. J. Org. Chem. 1986; 51: 380
• 13a Williams DR, Brown DL, Benbow JW. J. Am. Chem. Soc. 1989; 111: 1923
• 13b Williams DR, Osterhout MH, McGill JM. Tetrahedron Lett. 1989; 30: 1327
• 14a Davies SG, Nicholson RL, Price PD, Roberts PM, Russell AJ, Savory ED, Smith AD, Thomson JE. Tetrahedon: Asymmetry 2009; 20: 758
• 14b Davies SG, Lee JA, Roberts PM, Thomson JE, West CJ. Tetrahedron 2012; 68: 4302
• 14c Brock EA, Davies SG, Lee JA, Roberts PM, Thomson JE. Org. Lett. 2012; 14: 4278
• 15 Aida T, Legault R, Dugat D, Durst T. Tetrahedron Lett. 1979; 20: 4993
• 16 Knapp S, Rodriques KE, Levorse AT, Omaf RM. Tetrahedron Lett. 1985; 26: 1803
• 17 Bartlett PA. Tetrahedron 1980; 36: 2
• 18 Takahata H, Takamatsu T, Mozumi M, Chen Y.-S, Yamazaki T, Aoe K. J. Chem. Soc., Chem. Commun. 1987; 1627
• 19 Diaba F, Bonjoch J. Chem. Commun. 2011; 47: 3251
• 20a Corey EJ, Shibasaki M, Knolle J. Tetrahedron Lett. 1977; 18: 1625
• 20b Hirama M, Uei M. Tetrahedron Lett. 1982; 23: 5307
• 20c Tamaru Y, Mizutani M, Furukawa Y, Kawamura S, Yoshida Z, Yanagi K, Minobe M. J. Am. Chem. Soc. 1984; 106: 1079
• 20d Murata S, Suzuki T. Chem. Lett. 1987; 849
• 20e Kitagawa O, Hanano T, Hirata T, Inoue T, Taguchi T. Tetrahedron Lett. 1992; 33: 1299
• 20f Hirama M, Iwashita M, Yamazaki Y, Ito S. Tetrahedron Lett. 1984; 25: 4963
• 20g Biloski AJ, Wood RD, Ganem B. J. Am. Chem. Soc. 1982; 104: 3233
• 20h Kitagawa O, Taguchi T. Synlett 1999; 1191
• 21a Kitagawa O, Suzuki T, Taguchi T. Tetrahedron Lett. 1997; 38: 8371
• 21b Kitagawa O, Suzuki T, Taguchi T. J. Org. Chem. 1998; 63: 4842
• 22 Mizar P, Burrelli A, Günther E, Softje M, Farooq U, Wirth T. Chem. Eur. J. 2014; 20: 13113
• 23 Cheyenne S, Brindle CS, Yeung CS, Jacobsen EN. Chem. Sci. 2013; 4: 2100
• 24 Kim KK, Lee YJ, Kim JK, Sung DK. Chem. Commun. 2002; 1116
• 25a Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X. Angew. Chem. 2010; 122: 6296 ; Angew. Chem. Int. Ed. 2010, 49, 6160
• 25b Cai Y, Liu X, Jiang J, Chen W, Lin L, Feng X. J. Am. Chem. Soc. 2011; 133: 5636
• 25c Cai Y, Liu X, Li J, Chen W, Wang W, Lin L, Feng X. Chem. Eur. J. 2011; 17: 14916