9. References and Notes Scheme 26. Synthesis of Tarchonanthuslactone. (†) This review is dedicated to Professor Herbert C. Brown on his ninetieth birthday. (1) (a) Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1956, 78, 5694. (b) Brown, H. C. Hydroboration; Benjamin: New York, 1962. (2) (a) Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, NY, 1972. (b) Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Scheme 27. Synthesis of Umuravumbolide. Scheme 28. Synthesis of Mevinolin Analogs via Ring-Closing Metathesis. 34 VOL. 35, NO. 1 • 2002 Syntheses via Boranes; Wiley & Sons: New York, 1975. (Reprinted as Volume 1 by <strong>Aldrich</strong> Chemical Co., 1999; catalog no. Z40,094-7). (c) Mikhailov, B. M.; Bubnov, Y. N. Organoboron Compounds in Organic Synthesis (English Translation); Harwood Academic Science Publishers: Utrecht, The Netherlands, 1984. (3) (a) Brown, H. C.; Zaidlewicz, M. Organic Syntheses via Boranes: Recent Developments; <strong>Aldrich</strong> Chemical Co.: Milwaukee, WI, 2001; Figure 7. HMG-CoA Reductase Inhibitors. Volume 2. (b) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988. (4) Organoboranes for Syntheses; Ramachandran, P. V., Brown, H. C., Eds.; ACS Symposium Series 783; American Chemical Society: Washington, DC, 2001. (5) Matteson, D. S. Stereodefined Synthesis with Organoboranes; Springer-Verlag: Berlin, 1995. (6) Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486. (7) (a) Brown, H. C.; Ramachandran, P. V. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI: Greenwich, CT, 1995; Volume 1, Chapter 5. (b) Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, 1. (c) Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1994, 66, 201. (d) Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1991, 63, 307. (e) Brown, H. C.; Singaram, B. Proc. Ind. Acad. Sci. 1988, 100, 119. (f) Brown, H. C.; Singaram, B. Acc. Chem. Res. 1988, 21, 287. (g) Srebnik, M.; Ramachandran, P. V. <strong>Aldrich</strong>imica Acta 1987, 20, 9. (8) Due to rapid developments in the area of allylboration, this short review is not exhaustive. Any omission is not intentional. For reviews of asymmetric allylborations using chiral allylboronates, see: (a) Hoffmann, R. W.; Neil, G.; Schlapbach, A. Pure Appl. Chem. 1990, 62, 1993. (b) Hoffmann, R. W. Pure Appl. Chem. 1988, 60, 123. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (d) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1982, 21, 555. (e) Roush, W. R. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Supplement E 21, Volume 3, p 1410. (f) Roush, W. R. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkin, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 14. (g) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Volume 2. (9) Mikhailov, B. M.; Bubnov, Y. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1964, 1874; Chem. Abstr. 1965, 62, 11840e. (10) Mikhailov, B. M.; Pozdnev, V. F. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 1477; Chem.
Abstr. 1968, 68, 29743j. (11) Reference 2(c), Part IV. (12) For a review on α-substituted allylboronates, see reference 8(e), p 1462. (13) (a) Hoffmann, R. W.; Zeiss, H.-J. J. Org. Chem. 1981, 46, 1309. (b) Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem., Int. Ed. Engl. 1979, 18, 306. (14) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293. (15) Fenzl, W.; Köster, R. Liebigs Ann. Chem. 1975, 1322. (16) For a review on the chemistry of diisopinocampheylboron enolates, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (17) Bubnov, Y. N. Pure Appl. Chem. 1991, 63, 361. (18) (a) Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 1529. (b) Brown, H. C.; Phadke, A. S.; Bhat, N. G. Tetrahedron Lett. 1993, 34, 7845. (19) Wuts, P. G. M.; Thompson, P. A.; Callen, G. R. J. Org. Chem. 1983, 48, 5398. (20) Brown, H. C.; Rangaishenvi, M. V.; Jayaraman, S. Organometallics 1992, 11, 1948. (21) Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789. (22) Sato, M.; Yamamoto, Y.; Hara, A.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7071. (23) Narla, G.; Brown, H. C. Tetrahedron Lett. 1997, 38, 219. (24) (a) Herold, T.; Schrott, U.; Hoffmann, R. W. Chem. Ber. 1981, 114, 359. (b) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (25) Haruta, R.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1982, 104, 7667. (26) Ikeda, N.; Arai, I.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483. (27) Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (28) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294. (29) Roush, W. R.; Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979. (30) Ditrich, K.; Bube, T.; Strumer, R.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1986, 25, 1028. (31) Chataigner, I.; Lebreton, J.; Zammattio, F.; Villiéras, J. Tetrahedron Lett. 1997, 38, 3719. (32) Reetz, M. T.; Zierke, T. Chem. Ind. 1988, 663. (33) Corey, E. J.; Yu, C.-M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495. (34) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (35) Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539. (36) Racherla, U. S.; Liao, Y.; Brown, H. C. J. Org. Chem. 1992, 57, 6614. (37) Kumar, D. J. S.; Madhavan, S.; Ramachandran, P. V.; Brown, H. C. Tetrahedron: Asymmetry 2000, 11, 4629. (38) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1987, 52, 319. (39) Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1997, 38, 2417. (40) (a) Chen, G. M.; Ramachandran, P. V.; Brown, H. C. Angew. Chem., Int. Ed. Engl. 1999, 38, 825. (b) Itsuno, S.; Watanabe, K.; Ito, K.; ElShehawy, A. A.; Sarhan, A. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109. (41) Brown, H. C.; Jadhav, P. K.; Perumal, P. T. Tetrahedron Lett. 1984, 25, 5111. (42) Brown, H. C.; Jadhav, P. K. Tetrahedron Lett. 1984, 25, 1215. (43) Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560. (44) (a) Hoffmann, R. W.; Kemper, B. Tetrahedron Lett. 1981, 22, 5263. (b) Wuts, P. G. M.; Bigelow, S. S. J. Org. Chem. 1982, 47, 2498. (45) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535. (46) Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243. (47) Brown, H. C.; Narla, G. J. Org. Chem. 1995, 60, 4686. (48) Barrett, A. G. M.; Seefeld, M. A.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1053. (49) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. (50) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1987, 52, 3701. (51) Brown, H. C.; Randad, R. S. Tetrahedron 1990, 46, 4463. (52) Hu, S.; Jayaraman, S.; Oehlschlager, A. C. J. Org. Chem. 1996, 61, 7513. (53) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1985, 107, 2564. (54) Chen, G.-M.; Ramachandran, P. V. Tetrahedron: Asymmetry 1997, 8, 3935. (55) Brown, H. C.; Jadhav, P. K. J. Org. Chem. 1984, 49, 4089. (56) Brown, H. C.; Randad, R. S.; Bhat, K. S.; Zaidlewicz, M.; Racherla, U. S. J. Am. Chem. Soc. 1990, 112, 2389. (57) (a) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831. (b) Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Soderquist, J. A.; Matos, K.; Burgos, C. H.; Lai, C.; Vaquer, J.; Medina, J. R.; Huang, S. D. In reference 4, Chapter 13. (58) For a list of applications of Ipc-derived allyland crotylboration, see references 7(a) and 7(b). (59) Epothilone A: Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Roschangar, F.; Sarabia, F.; Ninkovic, S.; Yang, Z.; Trujillo, J. I. J. Am. Chem. Soc. 1997, 119, 7960. (60) Nystatin A1: Nicolaou, K. C.; Anh, K. H. Tetrahedron Lett. 1989, 30, 1217. (61) Tetronasin: Ley, S. V.; Clase, J. A.; Mansfield, D. J.; Osbor, H. M. I. J. Heterocycl. Chem. 1996, 33, 1533. (62) Swinholide A: (a) Patron, A. P.; Richter, P. K.; Tomaszewski, M. J.; Miller, R. A.; Nicolaou, K. C. J. Chem. Soc., Chem. Commun. 1994, 1147. (b) Richter, P. K.; Tomaszewski, M. J.; Miller, R. A.; Patron, A. P.; Nicolaou, K. C. J. Chem. Soc., Chem. Commnun. 1994, 1151. (63) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. (64) For a review, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (65) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583. (66) For a recent review, see: Reddy, M. V. R.; Brown, H. C.; Ramachandran, P. V. In reference 4, Chapter 16. (67) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 739. (68) Reddy, M. V. R.; Yucel, A. J.; Ramachandran, P. V. J. Org. Chem. 2001, 66, 2512. (69) Ramachandran, P. V.; Reddy, M. V. R.; Rearick, J. P.; Hoch, N. Org. Lett. 2001, 3, 19. (70) (a) Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. I 1976, 1165. (c) Alberts, A. W.; Smale, T. C. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 3957. (71) (a) Sit, S. Y.; Parker, R. A.; Motoc, I.; Han, W.; Balasubramanian, N.; Catt, J. D.; Brown, P. J.; Harte, W. E.; Thompson, M. D.; Wright, J. J. J. Med. Chem. 1990, 33, 2982. (b) Stokker, G. E.; Hoffman, W. F.; Alberts, A. W.; Cragoe, E. J., Jr.; Deana, A. A.; Gilfillan, J. L.; Huff, J. W.; Novello, F. C.; Prugh, J. D.; Smith, R. L.; Willard, A. K. J. Med. Chem. 1985, 28, 347. (72) Reddy, M. V. R.; Ramachandran, P. V.; Brown, H. C. J. Organomet. Chem. 2001, 624, 239. (73) Contribution #17 from the Herbert C. Brown Center for Borane Research. DIP-Chloride and Alpine-Borane are a trademark and a registered trademark, respectively, of <strong>Sigma</strong>-<strong>Aldrich</strong> Co. About the Author P. V. Ramachandran (Chandran) received his Ph.D. degree in 1983 from the Indian Institute of Technology in Kanpur. In 1984, he joined Professor Herbert C. Brown’s group as a postdoctorate. After two years, he became Brown’s research assistant and continued in that position until 1997, when he joined the faculty of the Chemistry Department at Purdue University. He is a coauthor of nearly 100 research publications, including several reviews and book chapters. He has also edited two books. He currently supervises an 18-member research group at the Herbert C. Brown Center for Borane Research. Apart from chemistry, Chandran likes to visit historic sites with his wife and two sons. We offer P.V. Ramachandran’s latest book! Organoboranes for Syntheses P.V. Ramachandran and H.C. Brown, Eds., Oxford University Press, New York, NY, 2001, 264pp. Hardcover. This book examines the recent advances in the art of organic synthesis via organoboranes. The volume includes a wide range of topics in asymmetric synthesis, such as reduction, aldol reaction, allylboration, homologation, and cyclopropanation. Additional subjects include Suzuki coupling, amino acid synthesis, fluoro-organic synthesis, boron catalysts for stereoselective transformations, heterocyclic synthesis, and novel borohydride reagents. Z51,374-1 $115.00 VOL. 35, NO. 1 • 2002 35
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