Friedel-Crafts reaction of the Baylis-Hillman adducts of N-tosylimine derivatives

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6223-6226

  Lee, Hong Jung ^a   Seong, Mi Ra ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Baylis Hillman adducts; Friedel Crafts reaction; N Tosylimines

Indexed keywords

ALKENE; AMINE; BENZENE; CHLOROBENZENE; TOLUENE; XYLENE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0032552142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01280-5     Document Type: Article

References (16)

1. [1] Kim JN, Chung KH, Ryu EK. Tetrahedron Lett. 1994;35:903-904.
2. [2] Chung KH, Kim JN, Ryu EK. Tetrahedron Lett. 1994;35:2913-2914.
3. [3] Jennings WB, Lovely CJ. Tetrahedron 1991;47:5561-5568.
4. [4] Trost BM, Marrs C. J. Org. Chem. 1991;56:6468-6470.
5. [5] Boger DL, Corbett WL. J. Org. Chem. 1992;57:4777-4780.
6. [6] Boger DL, Corbett WL, Curran TT, Kasper AM. J. Am. Chem. Soc. 1991;113:1713-1729.
7. [7] Sisco J, Weinreb SM. Tetrahedron Lett. 1989;30:3037-3040.
8. [8] Sisco J, Weinreb SM. J. Org. Chem. 1990;55:393-395.
9. [9] Georg GI, Harriman GCB, Peterson SA. J. Org. Chem. 1995;60:7366-7368.
10. [10] Love BE, Raje PS, Williams TC II. Synlett 1994:493-494.
11. [11] Perlmutter P, Teo CC. Tetrahedron Lett. 1984;25:5951-5952.
12. [12] Kundig EP, Xu LH, Schnell B. Synlett 1994:413-414.
13. 3) δ 42.06 (benzyl carbon), 110.63, 118.60, 127.25, 128.58, 128.70, 128.79, 128.81, 130.02, 133.44, 136.36, 143.96.
14. 13C NMR data (see reference 14b); (a) Funabiki T, Hosomi H, Yoshida S, Tarama K. J. Am. Chem. Soc. 1982;104:1560-1568.
15. (b) Basavaiah D, Krishnamacharyulu M, Hyma RS, Pandiaraju S. Tetrahedron Lett. 1997;38:2141-2144.
16. [15] In the cases of 3e and 3f somewhat severe reaction conditions were needed to effect the reaction. This might be due to the preferential protonation at the methoxy group rather than at the tosylamide group, which makes protonation at the sulfonamide more difficult and also changes the extent of hydrogen bonding between the ester and sulfonamide functionality. In such a drastic reaction conditions, 3a gave only the E product 4aa. In addition, isomerization of 4aa to the corresponding Z isomer was not observed in the same reaction conditions of 3e-3f.