Z. Wang et al. / Journal of Organometallic Chemistry 646 (2002) 161–166
165
[
3] (a) D.A. Evans, L.K. Truesdale, Tetrahedron Lett. 14 (1973)
929;
b) D.A. Evans, L.K. Truesdale, G.L. Carroll, J. Chem. Soc.
Chem. Commun. (1973) 55;
c) A.E. Vougioukas, H.B. Kagan, Tetrahedron Lett. 28 (1987)
513;
4
(
(
5
(
(
d) M. Scholl, G.C. Fu, J. Org. Chem. 59 (1994) 7178;
e) J.K. Whitesell, R. Apodaca, Tetrahedron Lett. 37 (1996)
2
525;
f) T.P. Loh, K.C. Xu, D.S.C. Ho, K.Y. Sim, Synlett (1998)
169.
4] (a) Z. Guo-Fu, J. Mol. Catal. A: Chem. 132 (1998) 1381;
b) X. Zhou, J. Huang, P. Ko, K. Cheung, C. Che, J. Chem. Soc.
(
1
[
(
Dalton Trans. (1999) 3303.
[
[
5] P. Saravanan, A.R. Vijaya, V.K. Singh, Tetrahedron Lett. 39
(
1998) 3923.
6] (a) W.J. Greenlee, D.G. Hangauer, Tetrahedron Lett. 24 (1983)
559;
b) E. Abele, R. Abele, I. Mazheika, E. Lukevics, Chem. Hetero-
4
(
cycl. Compd. 35 (2000) 943.
[
[
7] (a) T. Miura, T. Masaki, J. Chem. Soc. Perkin Trans. 1 (1994)
Scheme 1.
1
(
2
659;
b) T. Miura, Y. Masaki, J. Chem. Soc. Perkin Trans. 1 (1995)
155.
(
3×20 ml). The organic layers were combined, washed
with brine (2×20 ml) and then dried over MgSO . The
8] (a) K. Higuchi, M. Onaka, Y. Izumi, J. Chem. Soc. Chem.
Commun. (1991) 1035;
4
solvent was removed with a rotary evaporator and then
under reduced pressure on a vacuum line to give the
crude product which was purified by flash chromatog-
raphy (hexane:ethyl acetate=10:1) to give the
cyanohydrin.
A typical procedure for the reaction of ketones with
TMSCN follows. To a solution of 1a (0.15 mmol) in
THF (2.0 ml) was added TMSCN (1.8 mmol) at room
temperature, followed by addition of the ketone (1.5
mmol). After the reaction conditions stated in Table 2
had been met, the solvent was removed under reduced
pressure on a vacuum line to give the crude product
which was purified by flash chromatography (hex-
ane:ethyl acetate=100:1) to give the cyanohydrin
silylether.
(
b) M. Onaka, K. Higuchi, K. Sugita, Y. Izumi, Chem. Lett.
(1989) 1393;
(c) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am.
Chem. Soc. 121 (1999) 2641.
[
9] (a) For a recent review see: M. North, Synlett. (1993) 807;
(
(
b) E.J. Corey, Z. Wang, Tetrahedron Lett. 34 (1993) 4001;
c) M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org.
Chem. 58 (1993) 1515;
(
(
5
(
Antonov, E. Vorontsov, V. Rozenberg, Tetrahedron Lett. 8
(1997) 3245;
(
(
(
d) C. Bolm, P. Muller, Tetrahedron Lett. 36 (1995) 1625;
e) M. Hayashi, T. Inoue, Y. Miyamato, N. Oguni, Tetrahedron
0 (1994) 4385;
f) Y. Belokon, M. Moscalenko, N. Ikonnikov, L. Yashkina, D.
g) H.C. Aspinall, N. Greeves, P.M. Smith, Tetrahedron Lett. 40
1999) 1763;
h) Y.N. Belokon, B Green, N.S. Ikonikov, M. North, V.I.
Tararov, Tetrahedron Lett. 40 (1999) 8147;
(
(
(
(
i) J. You, H. Gau, M.C.K. Choi, Chem. Commun. (2000) 1963;
j) I.P. Holmes, H.B. Kagan, Tetrahedron Lett. 41 (2000) 7457;
k) I.P. Holmes, H.B. Kagan, Tetrahedron Lett. 41 (2000) 7453;
l) J.M. Brunel, O. Legrand, G. Buono, Tetrahedron: Asymme-
Acknowledgements
try 10 (1999) 1979.
[10] K. Manju, S. Trehan, J. Chem. Soc. Perkin Trans. 1 (1995) 2383.
The authors thank the Donors of the Petroleum
Research Fund administered by the American Chemical
Society and the National Science Foundation for grant
support of this research and Dr P. Ilankumaran for
helpful discussions.
[
11] S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. (1991)
37.
12] (a) M.A.H. Laramay, J.G. Verkade, J. Am. Chem. Soc. 112
5
[
(
(
(
1990) 9421;
b) M.A.H. Laramay, J.G.. Verkade, Z. Anorg. Allg. Chem. 605
1991) 163.
[
13] P. Kisanga, J.G. Verkade, R. Schwesinger, J. Org. Chem. 65
2000) 5431.
(
References
[
[
14] T.-S. Tang, J.G. Verkade, J. Org. Chem. 59 (1994) 7793.
15] S. Arumugam, D. McLeod, J.G. Verkade, J. Org. Chem. 63
(1998) 3677.
[
[
1] W.P. Weber, Silicon Reagents for Organic Synthesis, Springer-
Verlag, Berlin, 1983 (and references cited therein).
2] (a) G. Jenner, Tetrahedron Lett. 40 (1999) 491;
[16] Z. Wang, J.G. Verkade, Heteroatom. Chem. 9 (1998) 687.
[17] X. Liu, J.G. Verkade, J. Org. Chem. 65 (2000) 4560.
[18] (a) S. Arumugam, J.G. Verkade, J. Org. Chem. 62 (1997) 4827;
(b) A.E. Wroblewski, J.G. Verkade, J. Org. Chem., in press.
[19] P. Kisanga, B. D’Sa, J.G. Verkade, Tetrahedron 57 (2001) 8047.
[20] P. Kisanga, B. D’Sa, X. Fei, J.G. Verkade, Syn. Commun., in
press.
(b) J.W. Faller, L.-L. Gunderson, Tetrahedron Lett. 34 (1993)
2
275;
(
(
c) M.T. Reetz, D.N.A. Fox, Tetrahedron Lett. 34 (1993) 1119;
d) J.-H. Gu, M. Okamoto, M. Terada, K. Mikami, T. Nakai,
Chem. Lett. (1992) 1169.