An efficient method for conversion of 1-alken-3-yl carbonates to 1- alkenes and 3-chloro-1-alkenes via allyltitaniums

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7513-7516

  Matsuda, Shin Ichiro ^a   An, Duk Keun ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenes; Halogens and compounds; Steroids and sterols; Titanium and compounds

Indexed keywords

CARBONIC ACID; TITANIUM;

ARTICLE; COLUMN CHROMATOGRAPHY; HYDROLYSIS; ISOMERISM; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497675     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01633-5     Document Type: Article

References (26)

1. [1] Reetz MT. Organotitanium Reagents in Organic Synthesis, Berlin/Heidelberg: Springer-Verlag, 1986. Yamamoto, Y.; Asao, N. Chem. Rev. 1993;93:2207-2293.
2. [1] Reetz MT. Organotitanium Reagents in Organic Synthesis, Berlin/Heidelberg: Springer-Verlag, 1986. Yamamoto, Y.; Asao, N. Chem. Rev. 1993;93:2207-2293.
3. [2] (a) Kasatkin A, Nakagawa T, Okamoto S, Sato F. J. Am. Chem. Soc. 1995;117:3881-3882.
4. (b) Gao Y, Sato F. J. Org. Chem. 1995;60:8136-8137.
5. (c) Kasatkin A, Sato F. Angew. Chem., Int. Ed. Engl. 1996;35:2848-2849.
6. (d) Hikichi S, Gao Y, Sato F. Tetrahedron Lett. 1997;38:2867-2870.
7. (e) Teng X, Kasatkin A, Kawanaka Y, Okamoto S, Sato F. Tetrahedron Lett. 1997;38:8977-8980.
8. [3] For the reaction with aldehydes, see references 2a, 2c, 2d and 2e. For the reaction with imines, see references 2b and 2d.
9. [4] Valkanas G, Waight ES. J. Am. Chem. Soc. 1959:2720-2727 and references cited therein.
10. [5] The reaction with NCS afforded a mixture of α-and γ-chlorinated products in a variable ratio because of instability of the resulting 3-chloro-3-aryl-1-propene which can easily rearrange to 1-chloro-3-aryl-2-propenes even under neutral conditions. See, ref. 4.
11. [6] For metal-catalyzed or -mediated regioselective conversion of allylic alcohol derivatives to alkenes, see: Pd-catalyzed reduction; (a) Tsuji J, Minami I, Shimizu I. Synthesis, 1986;623-627.
12. (b) Mandai T, Suzuki S, Murakami T, Fujita M, Kawada M, Tsuji J. Tetrahedron Lett. 1992;33:2987-2990.
13. (c) Mandai T, Matsumoto T, Kawada M, Tsuji J. J. Org. Chem. 1992;57:6090-6092.
14. (d) Mandai T, Matsumoto T, Kawada M, Tsuji J. Tetrahedron, 1994;50:475-486. Protonation of allylsamariums;
15. (e) Tabuchi T, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986;27:601-602.
16. (f) Yoshida A, Hanamoto T, Inanaga J, Mikami K. Tetrahedron Lett. 1998;39:1777-1780.
17. 2-butene) was reported to afford a mixture of two possible regioisomers. See: Ito H, Taguchi T, Hanzawa Y. Tetrahedron Lett. 1992;33:1295-1298.
18. [8] To the best of our knowledge, selective synthesis of tertiary allylic halides has not been reported.
19. 1H NMR analysis.
20. [10] Pregna-5,20-diene-3β-ol was identified as the aglycone of muricin from the Pacific gorgonian Muricea fruticosa, which displayed antifungal activity and specific inactivation of rabbit and rat liver cytochromes P-450. (a) Bandurraga MM, Fenical W. Tetrahedron, 1985;41:1057-65.
21. (b) Dawe RD, Wright JLC. Can. J. Chem. 1987;65:666-669.
22. (c) Halpert J, Jaw JY, Balfour C. Mol. Pharmacol. 1988;34:148-156.
23. 1H NMR data with those reported in the literature (ref. 10b).
24. [12] Diastereoselective Pd-catalyzed reduction of a similar substrate providing the corresponding 1-alkene has been reported, see ref. 6b.
25. [13] A similar transition state model as that shown in Fig. 1 has been used for explanation of the regioselective hydrolysis of allylsamarium compounds. See ref. 6f.
26. E2′ halodemetallation reactions of allenylstannyl compounds have been reported. Cochran JC, Kuivila HG. Organometallics, 1982;1:97-103 and references cited therein.