4160
2. (a) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607. (b) Kitagawa, O.; Izawa,
H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447. (c) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi,
T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (d) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967. (e) Hughes, A. D.;
Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295. (f) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi,
A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949. (g) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T.
Tetrahedron Lett. 1999, 40, 8827. (h) Bach, T.; Schröder, J.; Harms, K. Tetrahedron Lett. 1999, 40, 9003. (i) Curran, D. P.;
Liu, W.; Chen, C. H. J. Am. Chem. Soc. 1999, 121, 11012.
3. (a) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1996, 37, 5577. (b) Clayden, J.; Westlund, N.; Wilson, F. X.
Tetrahedron Lett. 1999, 40, 3329. (c) Clayden, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 949. (d) Bragg, R. A.; Clayden, J.
Tetrahedron Lett. 1999, 40, 8323. (e) Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8327. (f) Clayden, J.; Westlund,
N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 7883.
4. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899. (b) Clayden, J.; Lai, L. W. Angew. Chem.,
Int. Ed. 1999, 38, 2556.
5. (a) Casarini, D.; Foresti, E.; Gasparrini, F.; Lunazzi, L.; Macciantelli, D.; Misiti, D.; Villani, C. J. Org. Chem. 1993, 58,
5674. (b) Casarini, D.; Lunazzi, L.; Gasparrini, F.; Villani, C.; Cirilli, M.; Gavuzzo, E. J. Org. Chem. 1995, 50, 97. (c)
Jennings, W. B.; Kochanewycz, M. J.; Lunazzi, L. J. Chem. Soc., Perkin Trans. 2 1997, 2271. (d) Baker, R. W.; Kyasnoor,
R. V.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 2 1998, 1333.
6. Lett, R.; Marquet, A. Tetrahedron Lett. 1974, 30, 3379.
7. (a) Oki, M. In Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Deerfield Beach, FL, 1985, 160.
(b) Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron
1998, 54, 13 277.
8. In contrast with our results, Clayden et al. have reported the reversal in stereoselectivity in each reaction of 2-formyl-1-
naphthamides with RMgX or RLi, which can be ascribed to a chelated (RMgX) or non-chelated (RLi) transition state, see:
Ref. 3a.
9. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
10. The MO calculation by the MOPAC93/PM3 method showed a similar optimized structure for 1d, the energy difference of
which from the less stable conformer was 1.81 kcal/mol.
11. The chelated transition state was also supported by the Mukaiyama aldol reaction of 1d in the presence of TiCl4 in contrast
to the result in the presence of monodentate BF3·OEt2. These results will be reported in due course.
12. Prepared from the reaction of 1-lithio-2-dimethoxymethylnaphthalene and the DAG-sulfinate and subsequent hydrolysis.
For the preparation of the DAG-sulfinate, see: (a) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
(b) Watanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron: Asymmetry 1999, 10, 737.
13. (a) Lockard, J. P.; Schroeck, C. W.; Johnson, C. R. Synthesis 1973, 485. (b) Durst, T.; LeBelle, M. J.; Elzen, R. V.; Tin,
K.-C. Can. J. Chem. 1974, 52, 761. (c) Sato, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. (d) Furukawa,
N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341.
14. The optical purity was confirmed by the HPLC analysis (Chiralcel OD-H).
15. (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Soai, K.; Kawase, Y.; Oshio, A.
J. Chem. Soc. Perkin Trans. 1 1991, 1613.