Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart · New York Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of β,γ-Unsaturated Ketones Adam Shih-Yuan Lee*, Shu-Huei Wang, Yu-Ting Chang, Shu-Fang ChuDepartment of Chemistry, Tamkang University, Tamsui, 251, TaiwanFax: +886(2)26223830; e-Mail: adamlee@mail.tku.edu.tw; Recommend Article Abstract Buy Article All articles of this category Abstract A reaction mixture of β,γ-unsaturated ketone and BF3·OEt2 in CH3OH was stirred at room temperature and β-methoxy ketone was produced in high yield. The β-amino ketone was obtained as the major product from a reaction mixture of β,γ-unsaturated ketone, AlCl3 and Ts-NH2 in CH2Cl2 at room temperature. This Lewis acid promoted β-substitution reaction mechanism was proposed as that the process occurred via in situ isomerization of β,γ-unsaturated ketone to α,β-unsaturated ketone followed by the 1,4-addition reaction. Key words β,γ-unsaturated ketone - β-amino ketone - β-methoxy ketone - α,β-unsaturated ketone - 1,4-addition reaction Full Text References References 1 Mann J. Nature (London) 1994, 367: 594 2 Panek JS. Jain NF. J. Org. Chem. 2001, 66: 2747 3 Schreiber SL. Science 1991, 251: 283 4 Corey EJ. Trybulski EJ. Melvin LS. Nicolaou KC. Secrist JA. Lett R. Scheldarke PW. Falck JR. Brunelle DJ. Haslanger MF. Kim S. Yoo S. J. Am. Chem. Soc. 1978, 100: 4618 5 Mukaiyama T. Narasaka K. Org. Synth. 1987, 65: 6 6 Evans DA. In Asymmetric Synthesis Vol. 3: Morrison JD. Academic Press, Inc.; New York: 1984. p.1-274 7 Rossiter BE. Swingle NM. Chem. Rev. 1992, 92: 771 8 Krause N. Gerold A. Angew. Chem., Int. Ed. Engl. 1997, 36: 186 9a Oare DA. Heathcock CH. Top. Stereochem. 1989, 19: 227 9b Oare DA. Heathcock CH. Top. Stereochem. 1991, 20: 87 10 Yoshikoshi A. Miyashita M. Acc. Chem. Res. 1985, 18: 284 11 Larock RC. Comprehensive Organic Transformations-A Guide to Functional Group Preparations 2nd ed.: John Wiley and Sons, Inc.; New York: 1999. Chap. 15. p.1567-1616 12 Lee AS.-Y. Lin L.-S. Tetrahedron Lett. 2000, 41: 8803 13 Mukai C. Hanaoka M. Kataoka O. Tetrahedron Lett. 1994, 35: 6899 14 Kernan MR. Tetrahedron Lett. 1987, 28: 2809 15 McDogal PG. J. Org. Chem. 1986, 51: 4494 16 Mahmoud EN. Phytochemistry 1985, 24: 369 17 Gupta RK. Phytochemistry 1977, 16: 1104 18 Xie W. Mirocha CJ. Wen Y. Cheong WJ. Pawlosky RJ. Agric. Food Chem. 1991, 39: 1757 19 Remuinan MJ. Pattenden G. Tetrahedron Lett. 2000, 41: 7367 20 Kaseda T. Kikuchi T. Kibayashi C. Tetrahedron Lett. 1989, 34: 4539 21 Bashwira S. Hootele C. Tetrahedron 1988, 44: 4521 22 Hocquemiller R. Tetrahedron 1977, 33: 645 23 Iida H. Fukuhara K. Murayama Y. Machiba M. Kikuchi T. J. Org. Chem. 1986, 51: 4701 24 Bordwell FG. Acc. Chem Res. 1988, 21: 456 25 Taft RW. Bordwell FG. Acc. Chem Res. 1988, 21: 463
