A gem-allyl dianion synthon in water

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 295-298

  Chen, Dong Li ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030068362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02156-6     Document Type: Article

References (24)

1. Thompson, C. M., Dianion Chemistry in Organic Synthesis, CRC Press, 1994.
2. Seebach, D.; Henning, R.; Lehr, F. Angew. Chem. Int. Ed. Engl. 1978, 17, 458.
3. For reviews on synthesis of 1,3-diols, see: Mori, Y. Yuki Gosei Kagaku Kyokaishi, 1990, 48, 1092; Feldman, K. S. Synlett. 1995, 217; Panek, J. S. Chemtracts: Org. Chem. 1992, 5, 188 and 193.
4. For reviews on synthesis of 1,3-diols, see: Mon, Y. Yuki Gosei Kagaku Kyokaishi, 1990, 48, 1092; Feldman, K. S. Synlett. 1995, 217; Panek, J. S. Chemtracts: Org. Chem. 1992, 5, 188 and 193.
5. For reviews on synthesis of 1,3-diols, see: Mon, Y. Yuki Gosei Kagaku Kyokaishi, 1990, 48, 1092; Feldman, K. S. Synlett. 1995, 217; Panek, J. S. Chemtracts: Org. Chem. 1992, 5, 188 and 193.
6. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
7. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
8. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
9. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
10. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
11. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
12. For general reviews on organic reactions in aqueous medium, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis , 1994, 741; For reviews on Diels-Alder type reactions in aqueous medium see: Breslow, R. Acc. Chem. Res. 1991, 24, 159; Grieco, P. A. Aldrichim. Acta 1991, 24, 59; For reviews on Transition metal catalyzed reactions in aqueous medium, see: Herman, W. A.; Kohlpaintner, C. W. Angew. Chem. Int., Ed. Engl. 1993, 32, 1524; Kuntz, E. G. Chemtech, September 1987, p.570; Kalck, P.; Monteil, F. in Advances in Organometallic Chemistry, Vol 34, P. 219.
13. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
14. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
15. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
16. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
17. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
18. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
19. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
20. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
21. For other examples of indium mediated allylation reactions in aqueous medium, see: Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36 , 2721; Li, C. J. Tetrahedron Lett. 1995, 36, 517; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Isaac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Soc. 1995, 1003; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem 1994, 73-78; Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn., 1992, 65, 1736; Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647.
22. The structure was also confirmed chemically through PCC oxidation of the diol in which an ethylidene compound was generated. (equation presented)
23. Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Auge, J.; David, S. Tetrahedron Lett. 1983, 4009.
24. Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Auge, J.; David, S. Tetrahedron Lett. 1983, 4009.