Diastereoselective 'contra-Michael' addition of (-)- sparteine/organolithium complexes to secondary chiral cinnamyl amides

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3383-3386

  Bremand, Nathalie ^a   Marek, Ilan ^b   Normant, Jean F ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

( ) Sparteine; Alkyl lithium; Matched and mismatched pairs

Indexed keywords

2 BENZYLAMIDE; ALPHA METHYLBENZYLAMINE; BENZILIC ACID DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CINNAMIC ACID DERIVATIVE; CINNAMYLAMIDE; CUMENE; HYDROCHLORIC ACID; ORGANOLITHIUM COMPOUND; SPARTEINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0033597332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00495-5     Document Type: Article

References (16)

1. [1] Günther-Schmalz, H.-G. Comprehensive Organic Synthesis, Trost BM ; Fleming I, Schreiber SL Eds, Vol 4, New York: Pergamon Press, 1991: 199-232.
2. [2] a) Soai, K. ; Machida, H. ; Yokota, N. J. Chem. Soc. Perkin Trans 1 1987, 1909-1914.
3. b) Soai, K. ; Ookawa, A. J. Chem. Soc. Perkin Trans 1 1986, 759-764.
4. c) Soai, K. ; Machida, H. ; Ookawa, A. J. Chem. Soc. Chem. Com. 1985, 469-470.
5. d) Soai, K. ; Ookawa, A. ; Nohara Y. Synt. Com.. 1983, 27-34.
6. [3] Mukaiyama, T ; Iwasawa, N. Chem. Lett. 1981, 45-47.
7. [4] Tomioka, K. ; Suenaga, T. ; Koga, K. Tetrahedron Lett. 1986, 27, 369-372.
8. [5] Bergdahl, M. ; Iliefski, T. ; Nilsson, M. ; Olsson, T. Tetrahedron Lett. 1995, 36, 3227-3230.
9. [6] a) Touet, J. ; Baudoin, S.; Brown, E. Tetrahedron Asym. 1992, 3, 587-590.
10. b) Touet, J. ; Le Grumelec C. ; Huet, F. ; Brown, E. Tetrahedron Asym. 1993, 4, 1469-1472.
11. c) Touet, J.; Baudouin, S. ; Brown, E. J. Chem. Research · 1996, 1246-1254.
12. d) Brown, E. ; Deroye, C. ; Touet, J. Tetrahedron Asym. 1998, 9, 1605-1614.
13. [7] Asano, Y. ; Iida, A. ; Tomioka, K. Tetrahedron Lett. 1997, 52, 8973-8976.
14. [8] Alexakis, A. ; Frutos, J. ; Mutti, S. ; Mangeney, P. J. Org. Chem. 1994, 59, 3326-3334.
15. [9] Soai, K. ; Hayashi, H. ; Shinozaki, A. ; Umebayashi, H. ; Yamada, Y. Bull. Chem. Soc. Jpn. 1987 , 60, 3450-3452.
16. [10] Myers, A. ; Yang, B.H. ; Kopecky, D.J. Tetrahedron Lett. 1996, 37, 3623-3627.