Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1369-1372

  Ishikawa, Teruhiko ^a   Aikawa, Toshiaki ^a   Mori, Yumiko ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 TRIMETHYLSILYLOXY 2 BUTENE; 1,5 DIEN 7 YNE; ALKENE DERIVATIVE; ALLYLTRIMETHYLSILANE; CATION; CHEMICAL COMPOUND; METHYL CHLORIDE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHIRALITY; CONFORMATION; HYBRID; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2442432587     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049847g     Document Type: Article

References (37)

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3. For reviews for allylation using allyltrimethylsilane, see: (a) Hosomi, A. Acc. Chem. Res. 1988, 21, 200-206. (b) Sakurai, H. Pure Appl. Chem. 1985, 57, 1759-1770. (c) Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto H., Eds.; Springer-Verlag: Berlin, Heidelberg, 1999; Vol. II, Chapter 27.
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8. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
9. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
10. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
11. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
12. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
13. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
14. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
15. For synthetically useful allylations of allyl, propargyl, or benzyl cations with no stereochemical consequences, see: (a) Cella, J. A. J. Org. Chem. 1982, 47, 2125-2130. (b) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211-4214. (c) Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167-1170. (d) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975-1978. (e) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788-789. (f) Yokozawa, T.; Furuhashi, K.; Natsume, H. Tetrahedron Lett. 1995, 36, 5243-5246. (g) Kaur, G.; Kaushik, M.; Trehan, S. Tetrahedron Lett. 1997, 38, 2521-2524. (h) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705-2707.
16. Ishikawa, T.; Okano, M.; Aikawa, T.; Saito, S. J. Org. Chem. 2001, 66, 4635-4642 : see also Ishikawa, T.; Aikawa, T.; Mon, Y.; Saito. S. Org. Lett. 2003, 5, 51-54.
17. Ishikawa, T.; Okano, M.; Aikawa, T.; Saito, S. J. Org. Chem. 2001, 66, 4635-4642 : see also Ishikawa, T.; Aikawa, T.; Mon, Y.; Saito. S. Org. Lett. 2003, 5, 51-54.
18. See the Supporting Information for details.
19. The sterically less demanding nature of an alkyne unit should be responsible for the Z-selective conjugated enyne formation; see ref 4.
20. -.
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29. One of reviewers suggested on the basis of the reviewer's own DFT calculations using the Gaussian program that the cyclic oxonium ion has much lower energy than the open-chain Z carbocation but, contrary to our structure, it is totally planar. Our own efforts for this issue are now being made using the Gaussian 03 program.
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31. For the principle of least motion, see: (a) Hine, J. J. Org. Chem. 1966, 31, 1236-1246. (b) Tee, O. S. J. Am. Chem. Soc. 1969, 34, 7144-7149. (c) Jochum, C.; Gasteiger, J.; Ugi, I. Angew. Chem. Int. Ed. Engl. 1980, 7, 495-574.
32. For the principle of least motion, see: (a) Hine, J. J. Org. Chem. 1966, 31, 1236-1246. (b) Tee, O. S. J. Am. Chem. Soc. 1969, 34, 7144-7149. (c) Jochum, C.; Gasteiger, J.; Ugi, I. Angew. Chem. Int. Ed. Engl. 1980, 7, 495-574.
33. 2 carbon took place to give β,γ-unsaturated ketones in a significant amount. These results suggest, though are not necessarily direct evidence, that we cannot completely ruled out the possibility of the 1,2-participation by the TBDMSO-group even for (E)-substrates.
34. (15) This compound was prepared from ethyl (S)-lactate through a series of reactions involving TBDMS protection, DIBALH reduction, Horner-Emmons reaction, and appropriate transformations directed to 3 as shown in Scheme 5.
35. Optically pure α-amino acids, α-hydroxycarboxylic acids, or glyceraldehyde were used for the preparation of 1 and 2: see the Supporting Information.
36. A series of routine transformations from α-amino acids involving deamination, esterification, O-protection, and reduction led to II.
37. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769-3772.