Catalytic asymmetric protonation of achiral lithium enolates mediated by a chiral tetraamine ligand with water as a proton source

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 209-213

  Yamashita, Yasuhiro ^a   Emura, Yoshihiro ^a   Odashima, Kazunori ^a   Koga, Kenji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric reactions; Catalysis; Cyclic ketones; Enantioselection; Enolates; Protonation

Indexed keywords

CITRIC ACID; KETONE; LIGAND; LITHIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PROTON TRANSPORT;

EID: 0034620203     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01912-7     Document Type: Article

References (24)

1. For recent reviews, see: (a) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566-2587. (b) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411-420.
2. For recent reviews, see: (a) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566-2587. (b) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411-420.
3. (a) Duhamel, L.; Plaquevent, J.-C. Tetrahedron Lett. 1977, 2285-2288.
4. (b) Duhamel, L.; Plaquevent, J.-C. J. Am. Chem. Soc. 1978, 100, 7415-7416.
5. In addition to the literatures cited in Ref. 1a,b, see the following examples for recent studies of catalytic enantioselective protonation: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (b) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792-2793. (c) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691-8694.
6. In addition to the literatures cited in Ref. 1a,b, see the following examples for recent studies of catalytic enantioselective protonation: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (b) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792-2793. (c) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691-8694.
7. In addition to the literatures cited in Ref. 1a,b, see the following examples for recent studies of catalytic enantioselective protonation: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (b) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792-2793. (c) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691-8694.
8. (a) Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35-38.
9. (b) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589-7592.
10. Yamashita, Y.; Odashima, K.; Koga, K. Tetrahedron Lett. 1999, 40, 2803-2806.
11. 4, filtered and concentrated in vacuo to give a crude oil, which was purified by column chromatography (silica gel 15 g, hexanes:ether=50:1) to afford the target compound as a pale yellow oil. This oil was analyzed by HPLC (Daicel Chiralcel OJ or OD-H) to determine the enantiomeric excess.
12. 7c are known. (a) Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 4667-4672. (b) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081-3087. (c) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
13. 7c are known. (a) Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 4667-4672. (b) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081-3087. (c) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
14. 7c are known. (a) Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 4667-4672. (b) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081-3087. (c) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
15. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
16. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
17. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
18. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
19. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
20. 8a-f For related discussions, see the following review articles and references cited therein: (a) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492. (b) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032. (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290. See also: (e) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253-10264. (f) Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342-9347.
21. The reproducibility of the protonation experiments under the catalytic conditions of entry 7 was that, although the ee ranged from 80 to 89%, the values close to 89% ee were obtained in most cases.
22. An additional fact supporting the effectiveness of water as a proton source is that the catalytic protonation with (R)-1 in place of (R,R)-2 under the catalytic condition of entry 11 also induced a moderate enantioselectivity (74% ee).
23. (a) Murakata, M.; Yasukata, T.; Aoki, T.; Nakajima, M.; Koga, K. Tetrahedron 1998, 54, 2449-2458.
24. (b) Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829-8830.