Chemistry Reference
In-Depth Information
aldehyde with BF 3 is attacked by the allyl moiety of the enantiopure allylsilane.
This can be considered to be the first demonstration of a remote steric effect of
the chiral substituent on the asymmetric Hosomi-Sakurai reaction.
References
1 Heathcock, C.H. (1984), in Asymmetric
Synthesis , vol. 3, ch. 2 (ed. J.D. Morrison),
Academic Press, Orlando, pp. 111-212.
2 Duthaler, R.O., Hafner, A., and Riediker,
M. (1990) Pure Appl. Chem. , 62 , 631-642.
3 (a) Duthaler, R.O. and Hafner, A. (1992)
Chem. Rev. , 92 , 807-832; (b) Kunz, H.
and Rück, K. (1993) Angew. Chem. Int.
Ed. Engl. , 32 , 336-358; (c) Boysen,
M.M.K. (2007) Chem. Eur. J. , 13 ,
8648-8659.
4 (a) Duthaler, R.O., Hafner, A., and
Riediker, M. (1991), in Organic Synthesis
Via Organometallics (eds K.H. Dötz and
R.W. Hoffmann), Vieweg, Braunschweig,
pp. 285-309; (b) Hafner, A., Duthaler,
R.O., Marti, R., Rihs, G., Rothe-Streit, P.,
and Schwarzenbach, F. (1992) J. Am.
Chem. Soc. , 114 , 285-309.
5 Duthaler, R.O., Herold, P., Lottenbach,
W., Oertle, K., and Riediker, M. (1989)
Angew. Chem. Int. Ed. Engl. , 28 ,
495-497.
6 (a) Masamune, S., Sato, T., Kim, B.M.,
and Wollmann, T.A. (1986) J. Am. Chem.
Soc. , 108 , 8279-8281; (b) Sort, R. and
Masamune, S. (1987) Tetrahedron Lett. ,
28 , 2841-2844.
7 (a) Reetz, M.T., Kunish, F., and
Heitmann, P. (1986) Tetrahedron Lett. , 27 ,
4721-4724; (b) Reetz, M.T. (1988) Pure
Appl. Chem. , 60 , 1607-1614; (c) Reetz,
M.T., Rivadeneira, E., and Niemeyer, C.
(1990) Tetrahedron Lett. , 31 , 3863-3866.
8 Oertle, K., Beyeler, H., Duthaler, R.O.,
Lottenbach, W., Riediker, M., and
Steiner, E. (1990) Helv. Chim. Acta , 73 ,
353-357.
9 Kashin, D., Meyer, A., Wittenberg, R.,
Schoning, K.-U., Kamlage, S., and
Kirschning, A. (2007) Synthesis , 304-319.
10 Amans, D., Bellosta, V., and Cossy, J.
(2007) Org. Lett. , 9 , 4761-4764.
11 (a) Li, Y., Paddon-Row, M.N., and Houk,
K.N. (1990) J. Org. Chem. , 55 , 481-493;
(b) Yamago, S., Machii, D., and
Nakamura, E. (1991) J. Org. Chem. , 56 ,
2098-2106; (c) Denmark, S.E. and
Henke, B.R. (1991) J. Am. Chem. Soc. ,
113 , 2177-2194.
12 (a) Reetz, M.T. and Peter, R. (1981)
Tetrahedron Lett. , 22 , 4691-4694; (b)
Reetz, M.T., Steinbach, R., and Kessler,
K. (1982) Angew. Chem. Int. Ed. Engl. , 21 ,
1899-1905; (c) Kuwajima, I. and
Nakamura, E. (1985) Acc. Chem. Res. , 18 ,
181-187; (d) Harrison, C.R. (1987)
Tetrahedron Lett. , 28 , 4135-4138; (e)
Panek, J.S. and Bula, O.A. (1988)
Tetrahedron Lett. , 29 , 1661-1664.
13 (a) Bold, G., Duthaler, R.O., and
Riediker, M. (1989) Angew. Chem. Int. Ed.
Engl. , 28 , 497-498; (b) Duthaler, R.O.,
Herold, P., Wyler-Helfer, S., and
Riediker, M. (1990) Helv. Chim. Acta , 73 ,
659-673.
14 Vuitel, L. and Jacot-Guillarmod, A. (1972)
Synthesis , 608-610.
15 (a) Ito, Y., Sawamura, M., and Hayashi,
T. (1986) J. Am. Chem. Soc. , 108 ,
6405-6406; (b) Hayashi, T., Uozumi, Y.,
Yamazaki, A., Sawamura, M.,
Hamashino, H., and Ito, Y. (1991)
Tetrahedron Lett. , 32 , 2799-2802; (c)
Pastor, S.D. and Togni, A. (1989) J. Am.
Chem. Soc. , 111 , 2333-2334.
16 (a) Hoffmann, R.W. (1982) Angew. Chem.
Int. Ed. Engl. , 21 , 555-566; (b)
Yamamoto, Y. and Maruyama, K. (1982)
Heterocycles , 18 , 357-386; (c) Hoffman,
R.W. (1987) Angew. Chem. Int. Ed. Engl. ,
26 , 489-503; (d) Yamamoto, Y. (1987)
Acc. Chem. Res. , 20 , 243-249; (e) Hoppe,
D. (1984) Angew. Chem. Int. Ed. Engl. , 23 ,
932-948; (f) Mulzer, J., Kattner, L.,
Strecker, A.R., Schröder, C., Buschmann,
J., Lehmann, C., and Luger, P. (1991)
J. Am. Chem. Soc. , 113 , 4218-4229.
17 (a) Sato, F., Iida, K., Iijima, S., Moriya,
H., and Sato, M. (1981) J. Chem. Soc.,
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