The vinylogous intramolecular Morita-Baylis-Hillman reaction

Chemtracts

Volumn 15, Issue 9, 2002, Pages 490-497

  Zanardi, Franca ^a   Appendino, Giovanni ^a   Casiraghi, Giovanni ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; VINYL DERIVATIVE;

CHEMICAL BOND; CHEMICAL REACTION; MORITA BAYLIS HILLMAN REACTION; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 0036669363     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (22)

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12. Morita, K., Suzuki, Z., Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815. In this work the authors suggest to call the novel reaction as "carbinol addition."
13. Baylis, A.B., Hillman, M.E.D. German Patent 2155113, Celanese Corp., 1972; Chem. Abs. 1972, 77, 34174q.
14. Even if the authors of one of these articles refer to this issue as "regioselectivity," we prefer to use the term "chemoselectivity." Chemoselectivity is which group reacts; regioselectivity is where it reacts.
15. Indeed, similar selectivity has been observed in double Michael addition reactions. See: Saito, S., Hirohara, Y., Narahara, O., Moriwake, T. J. Am. Chem. Soc. 1989, 111, 4533.
16. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
17. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
18. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
19. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
20. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
21. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
22. Recent applications: (a) Kumaragurubaran, N., Juhl, K., Zhuang, W., Bogevig, A., Jorgensen, K.A. J. Am. Chem. Soc. 2002, 124, 6254; (b) Dickerson, T., Janda, K.D. J. Am. Chem. Soc. 2002, 124, 3220; (c) Tanaka, F., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 3510; (d) Cordova, A., Watanabe, S., Tanaka, F., Notz, W., Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1866; (e) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11283; (f) Betancort, J.M., Barbas III, C.F. Org. Lett. 2001, 3, 3737; (g) Bahmanyar, S., Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.