Enantioselective aldol reaction of trimethoxysilyl enol ether catalyzed by lithium binaphtholate

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3763-3765

  Nakajima, Makoto ^a   Orito, Yuya ^a,b   Ishizuka, Tadao ^a   Hashimoto, Shunichi ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; LITHIUM DERIVATIVE; NAPHTHOL DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY; WATER ANALYSIS;

EID: 7044232021     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048485+     Document Type: Article

References (38)

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8. Other recent examples of enantioselective aldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (b) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (e) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71-72. (f) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
9. Other recent examples of enantioselective aldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (b) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (e) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71-72. (f) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
10. Other recent examples of enantioselective aldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (b) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (e) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71-72. (f) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
11. Other recent examples of enantioselective aldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (b) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (e) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71-72. (f) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
12. Other recent examples of enantioselective aldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420. (b) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319-9320. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. (e) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71-72. (f) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395-2396. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
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32. Monolithium salt of 3,3′-dibromobinaphthol gave syn adduct predominantly in moderate yield (42%, syn:anti = 1.8:1) with low enantioselectivity (27% ee (syn), 14% ee (anti)).
33. 2 column chromatography afforded the corresponding aldol adduct (90 mg, 94%) as a mixture of diastereomers.
34. Initial product under anhydrous conditions is the silyl ether of the corresponding aldol adduct, whereas silyl ether was not observed under aqueous conditions. The reaction with 0.5 equiv (to silyl enol ether) of water gave a 1:1 mixture of the silyl ether and the alcohol.
35. 16 95, 2.6:1, (69, 38); R = Cl, 98, 3.0:1, (78, 48); R = I, 98, 2.9:1, (73, 35).
36. D +657° (c 1.0, THF), mp 235-237°C. See: Kobayashi, S.; Ishitani, H. Jpn. Patent, JP 2001139508, 2001; Chem. Abstr. 2001, 134, 366697 and Supporting Information.
37. Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832-834.
38. Prepared from lithium enolate of cyclohexanone and commercially available chlorotriethoxysilane.