Direct chlorohydrin and acetoxy alcohol synthesis from olefins promoted by a Lewis acid, bis(trimethylsilyl) peroxide and (CH3)3SiX [16]

Journal of the American Chemical Society

Volumn 122, Issue 6, 2000, Pages 1245-1246

  Sakurada, Isao ^a   Yamasaki, Shingo ^a   Göttlich, Richard ^a   Iida, Takehiko ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALPHA CHLOROHYDRIN; TRIMETHYLSILYL DERIVATIVE;

COMPLEX FORMATION; LETTER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 0034673307     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993492s     Document Type: Letter

References (26)

1. (a) Suzuki, M.; Takada, H.; Noyori, R. J. Org. Chem. 1982, 47, 902-904.
2. (b) Matsubara, S.; Takai, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 2029-2032.
3. (c) Göttlich, R.; Yamakoshi, K.; Sasai, H.; Shihasaki, M. Synlett 1997, 971-973.
4. For chlorohydrin synthesis from olefins, see: Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; 325-326.
5. See Supporting Information for experimental details.
6. The stereochemistry was unequivocally determined by converting to (1R*,2S*,4R*,5S*)-1,2-bis(tert- butyldiphenylsilyloxymethyl)-4,5-epoxycyclohexane, whose structure is known by X-ray analysis. Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784. For the determination of the relative stereochemistry of other compounds, see Supporting Information.
7. Dehnicke, V. K. Z. Anorg. Allg. Chem. 1961, 308, 72-78.
8. For the discussion of oligomeric structure of oxotin complexes, see: Davies, A. G.; Smith, P. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Chapter 11, Vol. 2, p 519.
9. 2 gave less satisfactoy results in terms of reaction rate.
10. For the reactivity of a Sn-O bond, see ref 6.
11. 9 was not detected by NMR.
12. 3 gave the trans-azidohydrin (48%) and 1a (17%).
13. Wilson, C. V. In Organic Reactions: Adams, R., Ed.; John Willey & Sons Inc. New York, 1957; Chapter 6, Vol. 9, p 350.
14. n, gave less satisfactory results.
15. Metal-catalyzed epoxidation of olefins by BTSP: Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. Yudin, A. K.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 11536-11537.
16. Metal-catalyzed epoxidation of olefins by BTSP: Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256. Yudin, A. K.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 11536-11537.
17. 6b and 7b were found to be kinetic products: see Supporting Information.
18. 2Zr=O, BTSP, and TMSOAc gave the epoxide (26%) and 1b (3%) for 48 h, and 1b (73%) and the epoxide (20%) for 498 h.
19. For a catalytic asymmetric synthesis of chlorohydrins from olefins, see: (a) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791.
20. (b) Hamed, O.; Henry, P. M. Organometallics 1998, 17, 5184-5189.
21. For a catalytic asymmetric synthesis of halohydrins from epoxides, see: (a) Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428-2429.
22. (b) Nugent, W. A. J. Am. Chem. Soc. 1998, 120, 7139-7140.
23. The absolute configuration of 1S,2S-1a was determined by the comparison of the optical rotation; Fukazawa, T.; Shimoji, Y.; Hashimoto, T. Tetrahedron Asymmetry 1996, 7, 1649-1658. The absolute configuration of 1S,2S-2a was determined by the Mosher method; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
24. The absolute configuration of 1S,2S-1a was determined by the comparison of the optical rotation; Fukazawa, T.; Shimoji, Y.; Hashimoto, T. Tetrahedron Asymmetry 1996, 7, 1649-1658. The absolute configuration of 1S,2S-2a was determined by the Mosher method; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
25. The following results for 1a were obtained using other tartaric acid derivatives, dimethyl L-tartrate (64% yield, 45% ee); diethyl L-tartrate (58% yield, 51% ee); di-tert-butyl L-tartrate (24% yield, 18% ee); N,N,N′,N′-tetramethyl-L-tartaramide (12% yield, 2% ee).
26. 2O (both in 70% yields).