Direct, practical, and powerful crossed aldol additions between ketones and ketones or aldehydes utilizing environmentally benign TiCl4-Bu3N reagent

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8269-8280

  Tanabe, Yoo ^a   Matsumoto, Noriaki ^a   Higashi, Takahiro ^a   Misaki, Tomonori ^a   Itoh, Tomotaka ^a   Yamamoto, Misako ^a   Mitarai, Kumi ^a   Nishii, Yoshinori ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

Aldol addition; Chlorotrimethylsilane; Muscone; Titanium chloride; Tributylamine

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; MUSCONE; REAGENT; TITANIUM DERIVATIVE;

ALDOL REACTION; ALKYLATION; ANALYTIC METHOD; ARTICLE; HYDROGENATION; ISOMER; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

FELIS CATUS;

EID: 0037037849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00977-8     Document Type: Article

References (20)

1. (a) Heathcock C.H. Trost B.M., Fleming I., Comprehensive Organic Synthesis. Vol. 2:1991;181 (b) Smith M.B., March J. March's Advanced Organic Chemistry. 5th ed. 2001;Wiley, New York. p 1218.
2. (a) Heathcock C.H. Trost B.M., Fleming I., Comprehensive Organic Synthesis. Vol. 2:1991;181 (b) Smith M.B., March J. March's Advanced Organic Chemistry. 5th ed. 2001;Wiley, New York. p 1218.
3. (a) Mukaiyama T., Banno K., Narasaka K. Chem. Lett. 1973;1011. J. Am. Chem. Soc. 1974, 96, 7503 (b) Mukaiyama T. Organic Reactions. Vol. 28:1982;Wiley, New York. p 203 (c) Reetz M.T. Organotitanium Reagents in Organic Synthesis. 1986;Springer, New York, (d) Masamune S., Choy W., Peterson J.S., Rita L.R. Angew. Chem., Int. Ed. Engl. 24:1985;1 (e) Bosnich B. Aldrichim. Acta. 31:1998;76 (f) Corey E.J., Lee T.W. Chem. Commun. 2001;1321. For recent representative works: (g) Saito S., Hatanaka K., Kano T., Yamamoto H. Angew. Chem. Int. Ed. 37:1998;3378 (h) Schmittel M., Ghorai M.K., Haeuseler A., Henn W., Koy T., Soller R. Eur. J. Org. Chem. 1999;2007 (i) Mahrwald R., Ziemer B. Tetrahedron. 55:1999;14005 (j) Han Z.F., Yorimitsu H., Shinokubo H., Oshima K. Tetrahedron Lett. 41:2000;4415 (k) Ghosh A.K., Kim J.H. Tetrahedron Lett. 42:2001;1227.
4. (a) Evans D.A., Clark J.S., Metternich R., Novack V.J., Sheppard G.S. J. Am. Chem. Soc. 112:1990;866 (b) Evans D.A., Urpi F., Somers T.C., Clark J.S., Bilodeau M.T. J. Am. Chem. Soc. 113:1990;8215 (c) Evans D.A., Rieger D.L., Bilodeau M.T., Urpi F. J. Am. Chem. Soc. 112:1991;1047 (d) Crimmis M.T., King B.W., Tabet E.A., Chaudhary K. J. Org. Chem. 66:2001;894.
5. A part of the preliminary results appeared in (a) Yoshida Y., Hayashi R., Sumihara H., Tanabe Y. Tetrahedron Lett. 38:1997;8727 (b) Yoshida Y., Matsumoto N., Hamasaki R., Tanabe Y. Tetrahedron Lett. 40:1999;4227.
6. Ruzicka L. Helv. Chim. Acta. 9:1926;715. Detailed references is cited in Tanaka K., Ushio H., Kawabata Y., Suzuki H. J. Chem. Soc., Perkin Trans. 1. 1991;1445.
7. Ref. 5a,b, and (a) Hamasaki R., Funakoshi S., Misaki T., Tanabe Y. Tetrahedron. 56: 2000;7423 (b) Tanabe Y., Hamasaki R., Funakoshi S. Chem. Commun. 2001;1674 (c) Tanabe Y., Makita A., Funakoshi S., Hamasaki R., Kawakusu T. Adv. Synth. Catal. 344: 2002;507.
8. Nakamura E., Kuwajima I. Tetrahedron Lett. 24:1983;3341. see also p 3343.
9. Iwasawa N., Mukaiyama T. Chem. Lett. 1987;463.
10. 2 at -78°C showed progressive appearance of enol carbon peak (δ 135.85 and 151.20) of the titanium enolate.
11. (a) Mukaiyama T., Haga T., Iwasawa N. Chem. Lett. 1982;1601 (b) Mukaiyama T., Yura T., Iwasawa N. Chem. Lett. 1985;809.
12. Curran D.P., Porter N.A., Giese B. Stereochemistry of Radical Reactions. 1996;VCH Publishers, Inc. New York.
13. For recent reviews: (a) Williams A.S. Synthesis. 1999;1707 (b) Kraft P., Bajgrowicz J.A., Denis C., Fráter G. Angew. Chem. Int. Ed. 39:2000;2980.
14. Tsuji J., Yamada T., Kaito M., Mandai T. Bull. Chem. Soc. Jpn. 53:1980;1417.
15. (a) Kamat V.P., Hagiwara H., Suzuki T., Ando M. J. Chem. Soc., Perkin Trans. 1. 1998;2253 (b) Louie J., Bielawski C.W., Grubbs R.H. J. Am. Chem. Soc. 123:2001;11312 (c) Fujimoto S., Yoshikawa K., Itoh M., Kitahara T. Biosci. Biotechnol. Biochem. 66:2002;1389.
16. Yoshida Y., Sakakura Y., Aso N., Okada S., Tanabe Y. Tetrahedron. 55:1999;2183.
17. Ogura, S.; Yamamoto, T. JP 94192161. Chem. Abstr. 1995, 122, 132836.
18. Its synthesis and structure-activity relationship will be reported in near future.
19. Humphrey G.R., Miller R.A., Pye P.J., Rossen K., Reamer R.A., Maliakal A., Ceglia S.S., Grabowski E.J.J., Volante R.P., Reider P.J. J. Am. Chem. Soc. 121:1999;11261.
20. Tanabe Y., Murakami M., Kitaichi K., Yoshida Y. Tetrahedron Lett. 35:1994;8409.