5 (a) H. C. Brown and P. K. Jadhav, J. Am. Chem. Soc., 1983, 105, 2092;
(b) H. C. Brown, P. K. Jadhav, K. S. Bhat and T. Perumal, J. Org.
Chem., 1986, 51, 432.
6 Other allylation methods used resulted in lower yields and enantiomeric
excess of the homoallylic alcohol 6. For references on the allylation
methods, see (a) Y. C. Teo, K. T. Tan and T. P. Loh, Chem. Commun.,
2005, 1318; (b) Y. C. Teo, J. D. Goh and T. P. Loh, Org. Lett., 2005, 7,
2743; (c) J. Lu, S. J. Ji, Y. C. Teo and T. P. Loh, Org. Lett., 2005, 7, 159.
7 K. P. Chan, Y. L. Hui, J. L.-T. Chan and T. P. Loh, J. Org. Chem.,
2007, in press.
Notes and references
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2 For other syntheses of (+)-SCH 351448, see (a) E. J. Kang, E. J. Cho,
Y. E. Lee, M. K. Ji, D. M. Shin, Y. K. Chung and E. Lee, J. Am. Chem.
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8 D. Seebach, E. Hungerbu¨hler, R. Naef, P. Schnurrenberger,
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9 H. C. Brown and K. S. Bhat, J. Am. Chem. Soc., 1986, 108, 5919.
10 J. Cossy, S. BouzBouz and A. H. Hoveyda, J. Organomet. Chem., 2001,
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3 For selected literature on the Prins cyclization, see (a) L. Coppi, A. Ricci
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D. Wang and T. H. Chan, Tetrahedron Lett., 1987, 28, 3441; (c) J. Yang,
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13 Palladium catalyzed reduction16 of 2 via a radical mechanism resulted in
an incomplete conversion to unconjugated aldehyde 2a. The failure to
separate the 2 and 2a rendered spectroscopic analysis very difficult.
14 A significant amount of unreacted homoallylic alcohol 3 was recovered
in the three entries (6 to 8) in Table 1. There are possibly other
competing reactions which degrade this reactive aldehyde 2a in the
presence of a Lewis acid before Prins cyclization can take place.
15 ACCN denotes 1,19-azobis(cyclohexane) carbonitrile, a synthetic
equivalent to AIBN.
16 B. H. Lipshutz, C. S. Ung and S. Sengupta, Synlett, 1989, 64.
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