Mukaiyama Aldol Reactions of Silyl Enolates Catalyzed by Iodine

Synthetic Communications

Volumn 34, Issue 6, 2004, Pages 1065-1070

  Phukan, Prodeep ^a  

^a GAUHATI UNIVERSITY   (India)

Author keywords

Aldehydes; Iodine; Ketones; Mukaiyama aldol; Silyl enol ether; Silyl keten acetal

Indexed keywords

1 [(TRIMETHYLSILYL)OXY] 1 CYCLOHEXENE; 1 [(TRIMETHYLSILYL)OXY] 1 PHENYLETHYLENE; 1 METHOXY 2 METHYL 1 (TRIMETHYLSILYLOXY) 1 PROPENE; 3 HYDROXY 3 METHYL 1 PHENYL 1 HEXANONE; ACETAL; ALDEHYDE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; IODINE; KETENE DERIVATIVE; KETONE; METHYL 3 HYDROXY 2,2 DIMETHYL 3 (4 NITROPHENYL)PROPANOATE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MUKAIYAMA REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 1842585835     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028638     Document Type: Article

References (30)

1. (a) Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973, 1011;
2. (b) Mukaiyama, T.; Benno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
3. (a) Ohki, H.; Wada, M.; Akiba, K. Tetrahedron Lett. 1988, 29, 4719;
4. (b) Kawai, M.; Onaka, M.; Izumi, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1237;
5. (c) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773;
6. (d) Roux, C.L.; Itoughmane, H.G.; Dubac, J.; Jaud, J.; Vignaux, P. J. Org. Chem. 1993, 58, 1835;
7. (e) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlet 1993, 472;
8. (f) Ishihara, K.; Hananki, N.; Yamamoto, H. Synlett 1993, 577;
9. (g) Ranu, B.C.; Chakrabarty, R. Tetrahedron 1993, 49, 5333;
10. (h) Reetz, M.T.; Fox, D.N.A. Tetrahedron Lett. 1993, 34, 1119;
11. (i) Van de Weghe, P.; Collin, J. Tetrahedron Lett. 1993, 34, 3881;
12. (j) Nakamura, H.; Matsuhashi, H.; Arata, K. Synlett 2000, 668;
13. (k) Li, W-D.Z.; Zhang, X-X. Org. Lett. 2002, 4, 3485;
14. (l) Nakamura, E.; Shimizu, M.; Kuwajima, I.; Sakata, J.; Yokoyama, K.; Noyori, Y. J. Org. Chem. 1983, 48, 932;
15. (m) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1983, 105, 1598.
16. (a) Yadav, J.S.; Reddy, B.V.S.; Rao, C.V.; Reddy, M.S. Synthesis 2003, 247;
17. (b) Karimi, B.; Golshani, B. Synthesis 2002, 784;
18. (c) He, Z.; Gao, G.; Hand, E.S.; Kispert, L.D.; Strand, A.; Liaaen-Jensen, S. J. Phys. Chem. A 2002, 106, 2520;
19. (d) Xu, X.; Zhang, Y. Synth. Commun. 2002, 32, 2643;
20. (e) Basu, M.K.; Samajdar, S.; Becker, F.F.; Banik, B.K. Syn. Lett. 2002, 319;
21. (f) Yadav, J.S.; Reddy, B.V.S.; Rao, C.V.; Rao, K.V. J. Chem. Soc. Perkin Trans. 1 2002, 1401;
22. (g) Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T.N.B. Tetrahedron Lett. 2002, 43, 879;
23. (h) Yadav, J.S.; Chand, P.K.; Anjaneyulu, S. Tetrahedron Lett. 2002, 43, 3783;
24. (i) Periana, R.A.; Mirinov, O.; Taube, D.J.; Gamble, S. Chem. Commun. 2002, 2376;
25. (j) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653;
26. (k) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H.J. Org. Chem. 2001, 66, 7527;
27. (l) Deka, N.; Sarma, J.C. J. Org. Chem. 2001, 66, 1947.
28. Vaino, A.R.; Szarek, W.A. Chem. Commun. 1996, 2351.
29. Sato, T.; Wakahara, Y.; Otera, J.; Noyaki, H. J. Am. Chem. Soc. 1991, 113, 4028.
30. Creger, P.L. Tetrahedron Lett. 1972, 79.