Direct Access to Functionalized Cyclic Enones Using Mannich, Morita-Baylis-Hillman and Elimination Reactions

Abstract

A series of highly functionalized cyclic enones were obtained from Mannich, Morita-Baylis-Hillman and elimination reaction with cyclic enones.

Morita-Baylis-Hillman - cyclic enones - aminals - Mannich reactions - concavine

References

1a Baylis AB, and Hillman MED. inventors; Ger. Offen. 2155113  .  Chem. Abstr. 1972, 77, 34174q

1b Morita K. Suzuki Z. Hirose H. Bull. Chem. Soc. Jpn.  1968,  41:  2815 

1c Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 

1d Langer P. Angew. Chem. Int. Ed.  2000,  39:  3049 

2a Tilly DP. Williams CM. Bernhardt PV. Org. Lett.  2005,  7:  5155 

2b Heim R. Wiedemann S. Williams CM. Bernhardt PV. Org. Lett.  2005,  7:  1327 

3 Porzelle A. Williams CM. Schwartz BD. Gentle IR. Synlett  2005,  2923 

4a Shi M. Li C.-Q. Tetrahedron: Asymmetry  2005,  16:  1385 

4b Shi M. Chen LH. Li C.-Q. J. Am. Chem. Soc.  2005,  127:  3790 ; and references therein

5 Sun S. Zhang Q. Liu Q. Kang J. Yin Y. Li D. Dong D. Tetrahedron Lett.  2005,  46:  6271 

6a Zhao L.-J. He HS. Shi M. Toy PH. J. Comb. Chem.  2004,  6:  680 

6b Ribiere P. Enjalbal C. Aubagnac J.-L. Yadav-Bhatnagar N. Martinez J. Lamaty F. J. Comb. Chem.  2004,  6:  464 

7 Balan D. Adolfsson H. Tetrahedron Lett.  2003,  44:  2521 

8 Ribiere P. Yadav-Bhatnagar N. Martinez J. Lamaty F. QSAR Comb. Sci.  2004,  23:  911 

9 Shi M. Xu Y.-M. Shi Y.-L. Chem. Eur. J.  2005,  11:  1794 ; and literature therein

10 Shi M. Zhao G.-L. Adv. Synth. Catal.  2004,  346:  1205 

11 Liu X. Chai Z. Zhao G. Zhu S. J. Fluorine Chem.  2005,  126:  1215 

12 Kozlov NS. Kovaleva VN. Vestsi Akad. Navuk B. SSR, Ser. Khim. Navuk  1979,  118 ; Chem. Abstr. 1979, 91, 56428s

13 Koldobsky AB. Milyutin IA. Kalinin VN. Dokl. Akad. Nauk  1992,  324:  1015 

14 Arnone A. Bava A. Fronza G. Nasini G. Ragg E. Tetrahedron Lett.  2005,  46:  8037 

15 For a general review, see: Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed.  1998,  37:  1044 

16a Kinast G. Tietze L.-F. Angew. Chem. Int. Ed. Engl.  1976,  15:  239 

16b Sielemann D. Keuper R. Risch N. J. Prakt. Chem.  1999,  341:  487 

17 For the reaction of bis(aminol) ethers under the same conditions, see: Buckley BR. Bulman Page PC. Heaney H. Sampler EP. Carley S. Brocke C. Brimble MA. Tetrahedron  2005,  61:  5876 

18 Heany H. Papageorgiu G. Wilkins RF. Tetrahedron  1997,  53:  2941 

19 2-(Hydroxymethyl)-3-methylcyclohex-2-enone was obtained using the method of Lou et al. in 25% yield: Lou S. Wang PG. Cheng J.-P. J. Org. Chem.  2004,  69:  555