2686
S. Singh et al. / Tetrahedron: Asymmetry 13 (2002) 2679–2687
Kumada, M. J. Org. Chem. 1983, 48, 281; (c) Marshall, J.
A.; Yanik, M. M. J. Org. Chem. 1999, 64, 3798.
14. (a) Dreher, S. D.; Hornberger, K. R.; Sarraf, S. T.;
Leighton, J. L. Org. Lett. 2000, 2, 3197; (b) Dimitrov, V.;
Kostova, K.; Hesse, M. Tetrahedron: Asymmetry 1994, 5,
1891.
20. (a) Hull, K. G.; Visnick, M.; Tautz, W.; Sheffron, A.
Tetrahedron 1997, 53, 12405; (b) Ng, P. L.; Lambert, J.
N. Synlett 1999, 11, 1749; (c) Raatz, D.; Innertsberger,
C.; Reiser, O. Synlett 1999, 1907; (d) Willoughby, C. A.;
Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
21. For a review, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023;
(b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J.
Chem. 1994, 72, 1181; (c) Cintas, P. Synlett 1995, 1087;
(d) for mechanistic studies, see: Chan, T. H.; Yang, Y. J.
Am. Chem. Soc. 1999, 121, 3228; (e) Araki, S.; Ito, H.;
Butsugan, Y. J. Org. Chem. 1988, 53, 1831; (f) Paquette,
L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917;
(g) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc.
1996, 118, 1931; (h) Fujiwara, N.; Yamamoto, Y. J. Org.
Chem. 1997, 62, 2318; (i) Paquette, L. A.; Mitzel, T. M.;
Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org.
Chem. 1997, 62, 4293; (j) Hirashita, T.; Kamei, T.; Horie,
T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem.
1999, 64, 172; (k) Paquette, L. A.; Rothaar, R. R. J. Org.
Chem. 1999, 64, 217; (l) Li, C. J.; Chan, T. H. Tetra-
hedron 1999, 55, 11149.
15. (a) Chiu, P.; Lautens, M. Stereoselective Heterocyclic
Synthesis; Metz, P., Ed.; Springer-Verlag: Berlin Heidel-
berg, 1999; Chapter 1; (b) Pozharskii, A. F.; Soldatenkov,
A. T.; Katritzky, A. R. Heterocycles in Life and Society;
John Wiley & Sons: Chichester, 1997; (c) Moreno-Manas,
M.; Pleixats, R. Advances in Heterocyclic Chemistry;
Katritzky, A. R., Ed.; Academic Press: California, 1996;
Vol. 66, Chapter 2; (d) Wu, Y.-C.; Chang, F.-R.; Duh,
C.-Y.; Wang, S.-K. Heterocycles 1992, 34, 667; (e) Myint,
S. H.; Cortes, A.; Laurens, A.; Hocquemiller, R.;
Lebeouf, M.; Cave, A.; Cotte, J.; Quero, A.-M. Phyto-
chemistry 1991, 30, 3335; (f) Jossang, A.; Dubaele, B.;
Cave, A.; Bartoli, M.-H.; Beriel, H. J. Nat. Prod. 1991,
54, 967; (g) Marshall, J. A.; Xie, S. J. Org. Chem. 1995,
60, 7230; (h) Marshall, J. A.; Liao, J. J. Org. Chem. 1998,
63, 5962.
22. Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann.
16. For recent reviews for allylmetal additions, see: (a) Den-
mark, S. E.; Almstead, N. G. Modern Carbonyl Chem-
istry; Otera, J., Ed.; Wiley-VCH; Weinheim, 2000;
Chapter 10; (b) Yamamoto, Y.; Asao, N. Chem. Rev.
1993, 93, 2207; (c) Evans, D. A.; Dart, M. J.; Duffy, J.
L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc.
1995, 117, 6619; (d) Keck, G. E.; Boden, E. P. Tetra-
hedron Lett. 1984, 25, 265; (e) Keck, G. E.; Abbott, D.
E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984,
25, 3927; (f) Keck, G. E.; Abbott, D. E.; Wiley, M. R.
Tetrahedron Lett. 1987, 28, 139; (g) Keck, G. E.; Savin,
K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem.
1994, 59, 7889.
17. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J.
Org. Chem. 1986, 51, 432; (b) Corey, E. J.; Yu, C.-M.;
Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495; (c) Roush,
W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143; (d)
Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-
Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114,
2321; (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989,
45, 1043; (f) Racherla, U. S.; Brown, H. C. J. Org. Chem.
1991, 56, 401; (g) Racherla, U. S.; Brown, H. C. J. Org.
Chem. 1992, 57, 6614.
18. (a) Loh, T.-P.; Zhou, J.-R.; Yin, Z. Org. Lett. 1999, 1855;
(b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34,
7827; (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C.
J. Org. Chem. 1993, 58, 6543; (d) Mikami, K.; Terada,
M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940; (e)
Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.;
Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001; (f)
Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12;
(g) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am.
Chem. Soc. 1993, 115, 8467; (h) Denmark, S. E.; Wynn,
T. J. Am. Chem. Soc. 2001, 123, 6199.
19. Some representative reviews and articles for enantioselec-
tive allylation are: (a) Marshall, J. A. Chemtracts-Organic
Chemistry 1996, 9, 280; (b) Cozzi, P. G.; Tagliavini, E.;
Umani-Ronchi, A. Gaz. Chim. Ital. 1997, 127, 247; (c)
Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed.
Engl. 1996, 35, 2363l; (d) Furuta, K.; Mouri, M.;
Yamamoto, H. Synlett 1991, 561.
Chem. 1994, 73.
23. (a) Roberts, S. M. Biocatalysts for Fine Chemicals Syn-
thesis; John Wiley & Sons: Chichester, 1999; (b) Jaeger,
K.-E.; Reetz, M. T. Trends Biotechnol. 1998, 16, 396; (c)
Silverman, R. B. The Organic Chemistry of Enzyme-Cat-
alyzed Reactions; Acedemic Press: USA, 2000; (d)
Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 1475;
(e) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39,
2226; (f) Stereoselective Biocatalysis; Patel, R. N., Ed.;
Marcel Dekker: New York, 1999; (g) Kadereit, D.; Wald-
mann, H. Chem. Rev. 2001, 101, 3367; (h) Enzymatic
Reactions in Organic Media, Koskinen, A. M. P.;
Klibanov, A. M., Eds.; Blackie Academic & Professional:
Glasgow, 1996; (i) Hydrolases in Organic Synthesis, Born-
scheuer, U. T.; Kazlauskas, R. J., Eds.; Wiley-VCH:
Weinheim, 1999.
24. Felpin, F. X.; Vo-Thanh, G.; Robins, R. J.; Villieras, J.;
Lebreton, J. Synlett 2000, 1646.
25. Girard, S.; Robins, R. J.; Villieras, J.; Lebreton, J. Tetra-
hedron Lett. 2000, 41, 9245.
26. Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett
2000, 1461.
27. For synthesis of non-racemic homopropargylic alcohols,
see: (a) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999,
64, 8214; (b) Marshall, J. A.; Adams, N. D. J. Org.
Chem. 1998, 63, 3812.
28. (a) Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; (b)
Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron
Lett. 1994, 35, 8323.
29. For enzymatic resolution of racemic homoallylic alco-
hols, see: (a) Master, H. E.; Newadkar, R. V.; Rane, R.
A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253; (b)
Adam, W.; Saha-Moller, C. R.; Schmid, K. S. Tetra-
hedron: Asymmetry 1999, 10, 315; (c) Bierstedt, A.; Stolt-
ing, J.; Frohlich, R.; Metz, P. Tetrahedron: Asymmetry
2001, 12, 3399; (d) Uenishi, J.; Hiraoka, T.; Hata, S.;
Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube,
H. J. Org. Chem. 1998, 63, 2481; (e) Morgan, B.;
Oehlschlager, A. C.; Stokes, T. M. J. Org. Chem. 1992,
57, 3231; (f) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org.
Chem. 1994, 59, 6018.