Journal of the American Chemical Society
Article
rather modest intrinsic facial bias. See: (e) Roush, W. R.; Palkowitz, A.
D.; Palmer, M. J. J. Org. Chem. 1987, 52, 316. (f) Roush, W. R.;
Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
(g) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54,
1570. (h) Kim, H.; Ho, S.; Leighton, J. L. J. Am. Chem. Soc. 2011, 133,
6517. (i) Gao, X.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2011, 133,
12795.
Scheme 4. Highly Diastereoselective Synthesis of the all-anti-
Stereopentad Fragment of (+)-Zincophorin Using
Mismatched Double Asymmetric Crotylboration of
Aldehyde 5k with Crotylmetal Reagent (S)-(E)-22
(4) (a) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed.;
Wiley-VCH: Weinheim, 2000; p 227. (b) Schetter, B.; Mahrwald, R.
Angew. Chem., Int. Ed. 2006, 45, 7506.
(5) (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B.
M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1. (b) Yamamoto, Y.;
Asao, N. Chem. Rev. 1993, 93, 2207. (c) Denmark, S. E.; Almstead, N.
G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH:
Weinheim, 2000; p 299. (d) Denmark, S. E.; Fu, J. Chem. Rev.
2003, 103, 2763. (e) Lachance, H.; Hall, D. G. Org. React. 2008, 73, 1.
(6) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem.,
Int. Ed. Engl. 1985, 24, 1.
(7) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
(8) (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968,
18, 2199. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61.
(9) (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105,
2092. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
(10) For selected examples: (a) Ogawa, A. K.; Armstrong, R. W. J.
Am. Chem. Soc. 1998, 120, 12435. (b) Roush, W. R.; Palkowitz, A. D.;
Ando, K. J. Am. Chem. Soc. 1990, 112, 6348. (c) Evans, D. A.; Kaldor,
S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112,
7001.
(11) Chen, M.; Roush, W. R. J. Am. Chem. Soc. 2011, 133, 5744.
(12) For synthetic applications of reagent (S)-(E)-22 and useful
transformations of the vinylstannane products, see: (a) Sun, H.;
Abbott, J. R.; Roush, W. R. Org. Lett. 2011, 13, 2734. (b) Yin, M.;
Roush, W. R. Tetrahedron 2011, 67, 10274. (c) Chen, M.; Roush, W.
R. Org. Lett. 2012, 14, 426.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and spectroscopic data for all new
compounds. This material is available free of charge via the
■
S
(13) Please see Supporting Information for details.
(14) (a) Chen, M.; Ess, D. H.; Roush, W. R. J. Am. Chem. Soc. 2010,
132, 7881. (b) Stewart, P.; Chen, M.; Roush, W. R.; Ess, D. Org. Lett.
2011, 13, 1478.
(15) For recent examples: (a) Fang, G. Y.; Aggarwal, V. K. Angew.
́
Chem., Int. Ed. 2007, 46, 359. (b) Canales, E.; Gonzalez, A. Z.;
AUTHOR INFORMATION
Corresponding Author
■
Soderquist, J. A. Angew. Chem., Int. Ed. 2007, 46, 397. (c) Gonzalez, A.
Z.; Roman, J. G.; Alicea, E.; Canales, E.; Soderquist, J. A. J. Am. Chem.
Soc. 2009, 131, 1269. (d) Chen, M.; Handa, M.; Roush, W. R. J. Am.
Chem. Soc. 2009, 131, 14602. (e) Kister, J.; DeBaillie, A. C.; Lira, R.;
Roush, W. R. J. Am. Chem. Soc. 2009, 131, 14174. (f) Ess, D. H.;
Kister, J.; Chen, M.; Roush, W. R. Org. Lett. 2009, 11, 5538. (g) Chen,
M.; Roush, W. R. Org. Lett. 2011, 13, 1992. (h) Kister, J.; Nuhant, P.;
Lira, R.; Sorg, A.; Roush, W. R. Org. Lett. 2011, 13, 1868.
(16) (a) Song, Z.; Lohse, A. G.; Hsung, R. P. Nat. Prod. Rep. 2009,
26, 560. (b) Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno,
M. P. J. Am. Chem. Soc. 1988, 110, 4368. (c) Guindon, Y.; Murtagh, L.;
Caron, V.; Landry, S. R.; Jung, G.; Bencheqroun, M.; Faucher, A.-M.;
Guerin, B. J. Org. Chem. 2001, 66, 5427. (d) Komatsu, K.; Tanino, K.;
Miyashita, M. Angew. Chem., Int. Ed. 2004, 43, 4341. (e) Defosseux,
M.; Blanchard, N.; Meyer, C.; Cossy, J. J. Org. Chem. 2004, 69, 4626.
(f) Harrison, T. J.; Ho, S.; Leighton, J. L. J. Am. Chem. Soc. 2011, 133,
7308.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Dedicated to Professor David A. Evans in honor of his 70th
birthday. Financial support provided by the National Institutes
of Health (GM038436) is gratefully acknowledged.
REFERENCES
■
(1) (a) Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod.
2003, 66, 1022. (b) Baerson, S. R., Ed. Polyketides, Biosynthesis,
Biological Activity, and Genetic Engineering; American Chemical Society:
Washington DC, 2006; p 296. (c) Omura, S., Ed. Macrolide Antibiotics.
Chemistry, Biology, and Practice, 2nd ed.; Academic Press: New York,
2002.
(2) (a) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
(b) Paterson, I.; Cowden, C. J.; Wallace, D. J. In Modern Carbonyl
Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; p 249.
(c) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera,
J., Ed.; Wiley-VCH: Weinheim, 2000; p 403. (d) Yeung, K. S.;
Paterson, I. Chem. Rev. 2005, 105, 4237.
(3) (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489.
(b) Hoffmann, R. W.; Dahmann, G.; Andersen, M. W. Synthesis 1994,
629. (c) Chemler, S. R.; Roush, W. R. J. Org. Chem. 1998, 63, 3800.
(d) Chemler, S. R.; Roush, W. R. J. Org. Chem. 2003, 83, 1319. For
enantioenriched aldehydes 5 without β-branches (e.g., R =
CH2OTBS), the intrinsic diastereofacial bias is only ∼1.5:1. Many
crotylmetal reagents have demonstrated the ability to overcome this
(17) (a) Miyashita, M.; Shiratani, T.; Kawamine, K.; Hatakeyama, S.;
Irie, H. Chem. Commun. 1996, 1027. (b) Torres, W.; Rodriguez, R. R.;
Prieto, J. A. J. Org. Chem. 2009, 74, 2447.
(18) (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
(b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
(19) (a) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108,
294. (b) Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. J. Org. Chem.
1987, 52, 316. (c) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz,
A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
(20) Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am.
Chem. Soc. 2005, 127, 8044.
3931
dx.doi.org/10.1021/ja300472a | J. Am. Chem. Soc. 2012, 134, 3925−3931