Guanidinium Ylide Mediated Aziridination from Arylaldehydes: Scope and Limitations in the Formation of Unactivated 3-Arylaziridine-2-carboxylates

Abstract

The scope and limitations of guanidinium ylide mediated aziridinations from arylaldehydes yielding unactivated 3-arylaziridine-2-carboxylates, applicable to asymmetric synthesis, are discussed.

Key words

aldehydes - asymmetric synthesis - chiral auxiliaries - esters­ - ylides

• References

• 1a Aube J In Comprehensive Organic Synthesis . Vol. 1. Trost BM, Fleming I. Pergamon; Oxford: 1991: 835
• 1b Rosen T In Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Pergamon; Oxford: 1991: 428
• 1c Kemp JE. G In Comprehensive Organic Synthesis . Vol. 7. Trost BM, Fleming I. Pergamon; Oxford: 1991: 469
• 1d Tanner D. Angew. Chem., Int. Ed. Engl. 1994; 33: 599
• 1e Osborn HM. I, Sweeney J. Tetrahedron: Asymmetry 1997; 18: 1693
• 1f Atkinson RS. Tetrahedron 1999; 55: 1519
• 1g Mitchinson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 2000; 2862
• 2a Tsuge O, Kanemasa S. Adv. Heterocycl. Chem. 1989; 45: 231
• 2b Padwa A In Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon; Oxford: 1991: 1085
• 2c Gothelf KV, Jorgensen KA. Chem. Rev. 1998; 98: 863
• 2d Ishikawa T. Heterocycles 2012; 85: 2837
• 3 Hada K, Watanabe T, Isobe T, Ishikawa T. J. Am. Chem. Soc. 2001; 123: 7705
• 4 Haga T, Ishikawa T. Tetrahedron 2005; 61: 2857
• 5a Wannaporn D, Ishikawa T. J. Org. Chem. 2005; 70: 9399
• 5b Wannaporn D, Ishikawa T, Kawahata M, Yamaguchi K. J. Org. Chem. 2006; 71: 6600
• 6a Khantikaew I, Takahashi M, Kumamoto T, Suzuki N, Ishikawa T. Tetrahedron 2012; 68: 878
• 6b Kondo Y, Suzuki N, Takahashi M, Kumamoto T, Masu H, Ishikawa T. J. Org. Chem. 2012; 77: 7988
• 6c Kojima H, Takahata C, Lemin D, Takahashi M, Kumamoto T, Nakanishi W, Suzuki N, Ishikawa T. Helv. Chim. Acta 2013; 96: 379
• 6d Takahashi M, Suzuki N, Ishikawa T. J. Org. Chem. 2013; 78: 3250
• 7a Manaka T, Nagayama S.-I, Desadee W, Yajima N, Kumamoto T, Watanabe T, Ishikawa T, Kawahata M, Yamaguchi K. Helv. Chim. Acta 2007; 90: 128
• 7b Hayashi Y, Kumamoto T, Nakanishi W, Kawahata M, Yamaguchi K, Ishikawa T. Tetrahedron 2010; 66: 3836
• 7c Kumamoto T, Suzuki K, Kim S.-K, Hoshino K, Takahashi M, Sato H, Iwata H, Ueno K, Fukuzumi M, Ishikawa T. Helv. Chim. Acta 2010; 93: 2109
• 8 Ishikawa T. Chem. Pharm. Bull. 2010; 58: 1555
• 9a Isobe T, Fukuda K, Ishikawa T. J. Org. Chem. 2000; 65: 7770
• 9b Isobe T, Fukuda K, Tokunaga T, Seki H, Yamaguchi K, Ishikawa T. J. Org. Chem. 2000; 65: 7774
• 9c Isobe T, Fukuda K, Yamaguchi K, Seki H, Tokunaga T, Ishikawa T. J. Org. Chem. 2000; 65: 7779
• 10a Isobe T, Ishikawa T. J. Org. Chem. 1999; 64: 5832
• 10b Isobe T, Ishikawa T. J. Org. Chem. 1999; 64: 6984
• 10c Isobe T, Ishikawa T. J. Org. Chem. 1999; 64: 6989
• 11a Isobe T, Fukuda K, Ishikawa T. Tetrahedron: Asymmetry 1998; 9: 1729
• 11b Isobe T, Fukuda K, Araki Y, Ishikawa T. Chem. Commun. 2001; 243
• 11c Ishikawa T, Araki Y, Kumamoto T, Seki H, Fukuda K, Isobe T. Chem. Commun. 2001; 245
• 11d Ishikawa T, Isobe T. Chem. Eur. J. 2002; 8: 552
• 11e Ishikawa T, Isobe T. Synth. Org. Chem. Jpn. 2003; 61: 60
• 11f Kumamoto T, Ebine K, Endo M, Araki Y, Fushimi Y, Miyamoto I, Ishikawa T, Isobe T, Fukuda K. Heterocycles 2005; 66: 347
• 11g Kitani Y, Kumamoto T, Isobe T, Fukuda K, Ishikawa T. Adv. Synth. Catal. 2005; 347: 1653
• 11h Wannaporn D, Ishikawa T. Mol. Diversity 2005; 9: 321
• 11i Ishikawa T, Kumamoto T. Synthesis 2006; 737
• 11j Ryoda A, Yajima N, Haga T, Kumamoto T, Nakanishi W, Kawahata M, Yamaguchi K, Ishikawa T. J. Org. Chem. 2008; 73: 133
• 11k Saito N, Ryoda A, Nakanishi W, Kumamoto T, Ishikawa T. Eur. J. Org. Chem. 2008; 2759
• 11l Zhang G, Kumamoto T, Heima T, Ishikawa T. Tetrahedron Lett. 2010; 51: 3927
• 11m Tokunou S, Nakanishi W, Kagawa N, Kumamoto T, Ishikawa T. Heterocycles 2012; 84: 1045
• 11n Ishikawa T, Heima T, Yoshida M, Kumamoto T. Helv. Chim. Acta 2014; 97: 307
• 12 Lloyd D, Millar RW. J. Chem. Soc., Chem. Commun. 1976; 266
• 13 For example, see: Davoli P, Moretti I, Prati F, Alper H. J. Org. Chem. 1999; 64: 518
• 14 Davoli P, Forni A, Moretti I, Prati F, Torre G. Tetrahedron 2001; 57: 1801 ; and references therein
• 15 Takahashi, M.; Suzuki, N.; Ishikawa, T.; Huang, H.-Y.; Chang, H.-S.; Chen, I.-S. unpublished results.
• 16a Larsen SB, Bang-Andersen B, Johansen TN, Jorgensen M. Tetrahedron 2008; 64: 2938
• 16b Palomo C, Aizpurua JM, Balentova E, Jimenez A, Oyarbide J, Fratila RM, Miranda JI. Org. Lett. 2007; 9: 101
• 17 Wattanasin S, Kathawala FG. Synth. Commun. 1992; 22: 1487
• 18a Casarrubios L, Perez JA, Brookhart M, Templeton JL. J. Org. Chem. 1996; 61: 8358
• 18b Irgolic KJ In Houben–Weyl . 4th ed., Vol. E12b; Klamann D. Thieme; Stuttgart: 1990: 150