Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

Abstract

A highly regioselective reaction between allylzinc bromide reagents and α,β-unsaturated oxime ethers for the one-step synthesis of the homoallylic amines is reported. This process is a regioselective 1,2-addition reaction providing a new γ-position with carbon–carbon bond formation. Furthermore, the reaction substrates are widely applicable and can be produced in a high yield.

Key words

regioselectivity - homoallylic amine - α,β-unsaturated oxime ether - organozinc reagent - 1,2-addition

• References

• 1a Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. Pergamon; Oxford: 1992
• 1b Tomioka K, Nagaoka Y. In Comprehensive Asymmetric Catalysis, Vol. III. Jacobsen EN, Pfaltz A, Yamamoto H. Springer; New York: 1999. Chap. 31
• 1c Feringa BL. Acc. Chem. Res. 2000; 33: 346
• 1d Tomioka K. In Modern Carbonyl Chemistry . Otera J. Wiley-VCH; Weinheim: 2000. Chap. 12
• 1e Sibi MP, Manyem S. Tetrahedron 2000; 56: 8033
• 1f Lipshutz BH. In Organometallics in Organic Synthesis, A Manual, 2nd ed. Schlosser M. Wiley; Chichester: 2002: 665-815
• 1g Tomioka K. In Comprehensive Asymmetric Catalysis . Jacobsen EN, Pfaltz A, Yamamoto H. Springer; New York: 2004. Supplement to Chap. 31.1, 109-124
• 2a Daly JW, Garraffo HM, Spande TF. In Alkaloids: Chemical and Biological Perspectives, Vol. 13: Pelletier S. W. Pergamon Press; New York: 1999: 1-161
• 2b Lawrence SA. Amines: Synthesis, Properties and Applications . Cambridge University Press; Cambridge: 2004
• 2c Vazzana I, Budriesi R, Terranova E, Ioan P, Ugenti MP, Tasso B, Chiarini A, Sparatore F. J. Med. Chem. 2007; 50: 334
• 2d Pu X, Ma D. J. Org. Chem. 2003; 68: 4400
• 3a Pace V, Castoldi L, Hoyos P, Sinisterra JV, Pregnolato M, Sanchez-Montero JM. Tetrahedron 2011; 67: 2670
• 3b Soeta T, Ishizaka T, Ukaji Y. J. Org. Chem. 2016; 81: 2817
• 3c Hirner S, Kolb A, Westmeier J, Gebhardt S, Middel S, Harms K, Zezschwitz PV. Org. Lett. 2014; 16: 3162
• 3d Tomioka K, Shioya Y, Nagaoka Y, Yamada K. J. Org. Chem. 2001; 66: 7051
• 3e Tomioka K, Okamoto T, Kanai M, Yamataka H. Tetrahedron Lett. 1994; 35: 1891
• 3f Moody CJ, Gallagher PT, Lightfoot AP, Slawin AM. Z. J. Org. Chem. 1999; 64: 4419
• 3g Soeta T, Kuriyama M, Tomioka K. J. Org. Chem. 2005; 70: 297
• 3h Tomioka K, Shindo M, Koga K. J. Am. Chem. Soc. 1989; 111: 8266
• 3i Shindo M, Koga K, Tomioka K. J. Org. Chem. 1998; 63: 9351
• 4a Matsumoto K, Koyachi K, Shindo M. Tetrahedron 2013; 69: 1043
• 4b Saha M, Carter RG. Org. Lett. 2013; 15: 736
• 4c Amat M, Perez M, Proto S, Gatti T, Bosch J. Chem. Eur. J. 2010; 16: 9438
• 4d Nielsen DK, Nielsen LL, Jones SB, Toll L, Asplund MC, Castle SL. J. Org. Chem. 2009; 74: 1187
• 4e Kuang Y, Liu X, Chang L, Wang M, Lin L, Feng X. Org. Lett. 2011; 13: 3814
• 5a Seebach D, Ertas M, Locher R, Schweizer WB. Helv. Chim. Acta 1985; 68: 264
• 5b Cooke MP. Jr. J. Org. Chem. 1986; 51: 1637
• 5c Tomioka K, Shindo M, Koga K. J. Org. Chem. 1990; 55: 2276
• 5d Tomioka K, Shindo M, Koga K. Tetrahedron Lett. 1990; 31: 1739
• 5e Xu F, Tillyer RD, Tschaen DM, Grabowski EJ. J, Reider PJ. Tetrahedron: Asymmetry 1998; 9: 1651
• 6a Delaye P.-O, Vasse J.-L, Szymoniak J. Org. Lett. 2012; 14: 3004
• 6b Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
• 7a Friestad GK, Mathies AK. Tetrahedron 2007; 63: 2541
• 7b Ding H, Friestad GK. Synthesis 2005; 2815
• 7c Wright DL, Schulte JP. II, Page MA. Org. Lett. 2000; 2: 1847
• 7d Oraa H, Stagies R, van der Marel GA, van Boom JH, Blechert S. J. Chem. Soc., Chem. Commun. 2000; 1501
• 7e Voigtmann V, Blechert S. Synthesis 2000; 893
• 7f Kazmaier U, Zumpe FL. Angew. Chem. Int. Ed. 1999; 38: 1468
• 7g Fang X, Johannsen M, Yao S, Gathergood N, Hazell RG, Jørgensen KA. J. Org. Chem. 1999; 64: 4844
• 7h Kobayashi S, Ishitani H. Chem. Rev. 1999; 99: 1069
• 7i Brown RC. D, Fisher M. J. Chem. Soc., Chem. Commun. 1999; 1547
• 7j Meester WJ. N, Rutjes FP. J. T, Hemkens PH. H, Hiemstra H. Tetrahedron Lett. 1999; 40: 1601
• 7k Bloch R. Chem. Rev. 1998; 98: 1407
• 7l Enders D, Reinhold U. Tetrahedron: Asymmetry 1997; 8: 1895
• 7m Anderson JC, Siddons DC, Smith SC, Swarbrick ME. J. Chem. Soc., Chem. Commun. 1995; 1835
• 7n Enders D, Schankat J, Klatt M. Synlett 1994; 795
• 7o Hart DJ, Ha D.-C. Chem. Rev. 1989; 89: 1447
• 8a Kandepedu N, Abrunhosa-Thomas I, Troin Y. Org. Chem. Front. 2017; 4: 1655
• 8b Ramachandran PV, Burghardt TE. Chem. Eur. J. 2005; 11: 4387
• 8c Puentes CO, Kouznetsov V. J. Heterocycl. Chem. 2002; 39: 595
• 8d Hayashi T, Yamamoto A, Ito Y, Nishioka E, Miura H, Yanagi K. J. Am. Chem. Soc. 1989; 111: 6301
• 8e Burgess K, Liu L, Pal B. J. Org. Chem. 1993; 58: 4758
• 8f Trost BM, Van Vranken DL. J. Am. Chem. Soc. 1993; 115: 444
• 8g Chiral Amine Synthesis: Methods, Developments and Applications. Nugent TC. Wiley-VCH; Weinheim: 2010
• 9a Andrews PC, Peatt AC, Raston CL. Green Chem. 2004; 6: 119
• 9b Chan TH, Lu W. Tetrahedron Lett. 1998; 39: 8605
• 9c Law MC, Cheung TW, Wong K.-Y, Chan TH. J. Org. Chem. 2007; 72: 923
• 9d Choucair B, Leon H, Mire MA, Lebreton C, Mosset P. Org. Lett. 2000; 2: 1851
• 9e Vilaivan T, Winotapan C, Banphavichit V, Shinada T, Ohfune Y. J. Org. Chem. 2005; 70: 3464
• 9f Bernardi L, Ceré V, Femoni C, Pollicino S, Ricci A. J. Org. Chem. 2003; 68: 3348
• 10a Pandiancherri S, Lupton DW. Tetrahedron Lett. 2011; 52: 671
• 10b Yamamoto Y, Komatsu T, Maruyama K. J. Org. Chem. 1985; 50: 3115
• 11 Yanada R, Okaniwa M, Kaieda A, Ibuka T, Takemoto Y. J. Org. Chem. 2001; 66: 1283
• 12a Billet M, Klotz P, Mann A. Tetrahedron Lett. 2001; 42: 631
• 12b Panek JS, Jain NF. J. Org. Chem. 1994; 59: 2674
• 12c Veenstra SJ, Schmid P. Tetrahedron Lett. 1997; 38: 997
• 12d Roux M, Santelli M, Parrain JL. Org. Lett. 2000; 2: 1701
• 13a Das B, Satyalakshmi G, Suneel K, Shashikanth B. Tetrahedron Lett. 2008; 49: 7209
• 13b Akiyama T, Iwai J, Onuma Y, Kagoshima H. Chem. Commun. 1999; 2191
• 13c Aspinall HC, Bissett JS, Greeves N, Levin D. Tetrahedron Lett. 2002; 43: 323
• 13d Yadav JS, Reddy BV. S, Reddy PS. R, Rao MS. Tetrahedron Lett. 2002; 43: 6245
• 13e Akiyama T, Onuma Y. J. Chem. Soc., Perkin Trans. 1 2002; 1157
• 13f Yadav JS, Reddy BV. S, Raju AK. Synthesis 2003; 883
• 13g Das B, Ravikanth B, Laxminarayana K, Rac BV. J. Mol. Catal. A: Chem. 2006; 253: 92
• 13h Nagarapu L, Paparaju V, Pathuri G, Kantevari S, Pakkiru RR, Kamalla R. J. Mol. Catal. A: Chem. 2007; 267: 53
• 13i Xie ZF, Li GL, Zhao G, Wang JD. Chin. J. Chem. 2009; 27: 925
• 13j Sharma RK, Samuelson AG. J. Chem. Sci. 2006; 118: 569
• 13k Andrade CK. Z, Oliveira GR. Tetrahedron Lett. 2002; 43: 1935
• 13l Keck GE, Enholm EJ. J. Org. Chem. 1985; 50: 146
• 13m Wang DK, Dai LX, Hou XL. Tetrahedron Lett. 1995; 36: 8649
• 13n Nishigaichi Y, Takuwa A, Naruta Y, Maruyama K. Tetrahedron 1993; 49: 7395
• 13o Marshall JA. Chem. Rev. 1996; 96: 31
• 14a Itsuno S, Watanabe K, Matsumoto T, Kuroda S, Yokoi A, El-Shehawy A. J. Chem. Soc., Perkin Trans. 1 1999; 2011
• 14b Itsuno S, Watanabe K, Ito K, El-Shehawy AA, Sarhan AA. Angew. Chem., Int. Ed. Engl. 1997; 36: 109
• 14c Watanabe K, Kuroda S, Yokoi A, Ito K, Itsuno S. J. Organomet. Chem. 1999; 581: 103
• 14d Kuznetsov NY, Tikhov RM, Strelkova TV, Bubnov YN. Org. Biomol. Chem. 2018; 16: 7115
• 14e Yus M, Gonzalez-Gomez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
• 14f Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595
• 14g Watanabe K, Ito K, Itsuno S. Tetrahedron: Asymmetry 1995; 6: 1531
• 14h Huo H.-X, Duvall JR, Huanga M.-Y, Hong R. Org. Chem. Front. 2014; 1: 303
• 14i Vieira EM, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 3332
• 14j Ramadhar TR, Batey RA. Synthesis 2011; 1321
• 15 Akiyama T, Iwai J. Synlett 1998; 273
• 16 Kobayashi S, Araki M, Yasuda M. Tetrahedron Lett. 1995; 36: 5773
• 17 Kissman HM, Tarbell DS, Williams J. J. Am. Chem. Soc. 1953; 75: 2959
• 18a Kulkarni NA, Chen K. Tetrahedron Lett. 2006; 47: 611
• 18b Kulkarni NA, Yao C.-F, Chen K. Tetrahedron 2007; 63: 7816
• 18c Wolan A, Joachimczak A, Budny M, Kozakiewicz A. Tetrahedron Lett. 2011; 52: 1195
• 18d Ritson DJ, Cox RJ, Berge J. Org. Biomol. Chem. 2004; 2: 1921
• 18e Miyabe H, Yamaoka Y, Naito T, Takemoto Y. J. Org. Chem. 2004; 69: 1415
• 18f Chen MZ, McLaughlin M, Takahashi M, Tarselli MA, Yang DX, Umemura S, Micalizio GC. J. Org. Chem. 2010; 75: 8948
• 18g Zhao LM, Zhang SQ, Jin HS, Wan LJ, Dou F. Org. Lett. 2012; 14: 886
• 19 Frankland E. Justus Liebigs Ann. Chem. 1849; 71: 171
• 20a Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
• 20b Stahl L, Smoliakova IP. In Comprehensive Organometallic Chemistry III, Vol. 2. Crabtree H, Mingos DM. P. Elsevier; Amsterdam: 2007. Chap. 2.06, 309-418
• 21a Knochel P, Jones P. Organozinc Reagents: A Practical Approach . Oxford University Press; New York: 1999: 354
• 21b Zhao LM, Jin HS, Wan LJ, Zhang LM. J. Org. Chem. 2011; 76: 1831
• 21c Chen M, Zheng XL, Li WQ, He J, Lei AW. J. Am. Chem. Soc. 2010; 132: 4101
• 21d Kobayashi K, Kondo Y. Org. Lett. 2009; 11: 2035
• 21e Son S, Fu GC. J. Am. Chem. Soc. 2008; 130: 2756
• 21f Luo LC, Zhang H, Duan H, Liu Q, Zhu LZ, Zhang T, Lei AW. Org. Lett. 2007; 9: 4571
• 21g Zou XZ, Qian MX, Hu Q, Negishi E. Angew. Chem. Int. Ed. 2004; 43: 2259
• 22a Zhang M, Hu Y.-Y, Zhang S.-L. Chem. Eur. J. 2009; 15: 10732
• 22b Pan J, Zhang M, Zhang S.-L. Org. Biomol. Chem. 2012; 10: 1060
• 22c Zheng S.-L, Zhang S.-L. RSC Adv. 2016; 6: 26437
• 23a Zhang Y.-M, Yan T.-L, Cheng W, Zuo J.-M, Zhao W.-J. Tetrahedron Lett. 2009; 50: 2925
• 23b Zhang Y.-M, Han M.-H, Yan T.-L. Synth. Commun. 2012; 42: 2689
• 23c Wipf P, Pierce JG. Org. Lett. 2005; 7: 3537
• 24 Wolan A, Joachimczak A, Budny M, Kozakiewicz A. Tetrahedron Lett. 2011; 52: 1195
• 25a Heckmann G, Niemeyer M. J. Am. Chem. Soc. 2000; 122: 4227
• 25b Tammiku-Taul T, Burk P, Tuulmets A. J. Phys. Chem. A. 2004; 108: 133
• 26 Aliyu AO. C, Salawu OW, Onoja PK. J. Chem. Pharm. Res. 2013; 5: 129
• 27 Unterhalt B, Eljabour S. Arch. Pharm. 1986; 319: 1146
• 28 Dubost E, Fossey C, Cailly T, Rault S, Fabis F. J. Org. Chem. 2011; 76: 6414
• 29 Kawamorita S, Miyazaki T, Ohmiya H, Iwai T, Sawamura M. J. Am. Chem. Soc. 2011; 133: 19310
• 30 Pramanik S, Reddy RR, Ghorai P. J. Org. Chem. 2015; 80: 3656