A pinene-based chiral auxiliary for α-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity

Author:

Pinheiro Sergio,Gonçalves Clara B.S.S.,de Lima Marcelo B.,de Farias Florence M.C.

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference18 articles.

1. (a) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. Engl. 2000, 39, 1353. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.

2. For some recent examples see: (a) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Ruzziconi, R. Chem. Lett. 2000, 38. (b) de Oliveira, A. R. M.; Simonelli, F.; Marques, F. D.; Clososki, G. C.; Aparecida, M.; Oliveira, F. C.; Lenz, C. A. Quı́m. Nova 1999, 22, 854. (c) Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093. (d) Liu, J.-F.; Abiko, A.; Pei, Z.; Buske, D. C.; Masamune, S. Tetrahedron Lett. 1998, 39, 1873. (e) Schlessinger, R. H.; Petrus, L. H.; J. Org. Chem. 1998, 63, 9089. (f) Kashima, C.; Fukuchi, I.; Takahashi, K.; Fukusaka, K.; Hosomi, A. Heterocycles 1998, 47, 1357. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Seebach, D.; Hoffmann, M. Eur. J. Org. Chem. 1998, 1337. (i) Vicario, J. L.; Badia, D.; Dominguez, E.; Carrillo, L. Tetrahedron Lett. 1998, 39, 9267. (j) Ghosh, A. K.; Cho, H.; Onishi, M. Tetrahedron: Asymmetry 1997, 8, 821. (k) Ezquerra, J.; Rubio, A.; Martin, J.; Navio, J. L. G. Tetrahedron: Asymmetry 1997, 8, 669.

3. For Li enolates, see: (a) Fujita, M.; Laine, D.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1999, 1647. (b) Ahn, M.; Tanaka, K.; Fuji, J. Chem. Soc., Perkin Trans. 1 1998, 185. (c) Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malley, M. F.; Gougoutas, J. Z. Synlett 1998, 6, 664. (d) K. Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. For Si enolates, see: (e) Oppolzer, W.; Starkeman, C.; Rodriguez, I.; Bernardinelli, G. Tetrahedron Lett. 1991, 32, 61. (f) Oppolzer, W.; Blagg, J.; Rodriguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767. (g) Myers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672. (h) Genari, C.; Molinari, F.; Cozzi, P.; Oliva, A. Tetrahedron Lett. 1989, 30, 5163. (i) Oppolzer, W.; Marco-Contelles, J. Helv. Chim. Acta 1986, 69, 1699. (j) Genari, C.; Bernardi, A.; Colombo, L.; Scolastico, C. J. Am. Chem. Soc. 1985, 107, 5812. (k) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. For B enolates, see: (l) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586. (m) Yoshimitsu, T.; Song, J. J.; Wang, G.-Q.; Masamune, S. J. Org. Chem. 1997, 62, 8978. (n) Wang, Y.-C.; Hung, A.-W.; Chang, C.-S.; Yan, T.-H. J. Org. Chem. 1996, 61, 2038. (o) Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. (p) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. (q) Danda, H.; Hansen, M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173. For Ti enolates, see: (r) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527.

4. Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation

5. Farina, V.; Roth, G. P. Chem. Today 1999, 17, 39 and references cited therein.

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