Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Catalyzed Enantioselective Synthesis of Allyl Alcohols from Aldehydes and Alkenylboronic Acids Frank Schmidt, Jens Rudolph, Carsten Bolm*Institut für Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen, Germanye-Mail: Carsten.Bolm@oc.rwth-aachen.de; Recommend Article Abstract Buy Article All articles of this category Abstract Enantiomerically enriched (E)-allyl alcohols can be prepared in good yields by asymmetric alkenylation of aldehydes with alkenylboronic acids catalyzed by a chiral ferrocene-based agent. Key words C-C bond formation - allyl alcohols - enantioselective catalysis - vinylboronic acid - zinc organyls - vinylation Full Text References References 1a Bianchini C. Farnetti E. Glendenning L. Graziani M. Nardin G. Peruzzini M. Rocchini E. Zanobini F. Organometallics 1994, 14: 1489 1b Jeon J.-S. Li H. García C. LaRochelle LK. Walsh PJ. J. Org. Chem. 2005, 70: 448 1c Xie J.-H. Liu S. Huo X.-H. Cheng X. Duan H.-F. Fan B.-M. Wang L.-X. Zhou Q.-L. J. Org. Chem. 2005, 70: 2967 1d Noyori R. Ohkuma T. Angew. Chem. Int. Ed. 2001, 40: 40 ; Angew. Chem. 2001, 113, 40 1e Khai BT. Arcelli A. Tetrahedron Lett. 1996, 37: 6599 2a Oppolzer W. Radinov RN. Tetrahedron Lett. 1988, 29: 5645 2b Oppolzer W. Radinov RN. Tetrahedron Lett. 1991, 32: 5777 3 Kitamura M. Suga S. Kawai K. Noyori R. J. Am. Chem. Soc. 1986, 108: 6071 4a Oppolzer W. Radinov RN. Helv. Chim. Acta 1992, 75: 10 4b Oppolzer W. Radinov El-Sayed E. J. Org. Chem. 2001, 66: 4766 5 Dahmen S. Bräse S. Org. Lett. 2001, 25: 4119 6a Chen YK. Lurain AE. Walsh PJ. J. Am. Chem. Soc. 2002, 124: 12225 6b Lurain AE. Walsh PJ. J. Am. Chem. Soc. 2003, 125: 10677 6c Garcia C. Libra ER. Carroll PJ. Walsh PJ. J. Am. Chem. Soc. 2003, 125: 3210 6d Lurain AE. Carroll PJ. Walsh PJ. J. Org. Chem. 2003, 68: 1589 7 Ji J.-X. Qiu L.-Q. Yip C.-W. Chan ASC. J. Org. Chem. 2003, 68: 1589 8a Shibata T. Nakatsui K. Soai K. Inorg. Chim. Acta 1999, 296: 33 8b Soai K. Takahashi K. J. Chem. Soc., Perkin Trans. 1 1994, 1257 9 Tseng S.-L. Yang T.-K. Tetrahedron: Asymmetry 2005, 16: 773 10a Sprout CM. Richmond ML. Seto CT. J. Org. Chem. 2005, 70: 7408 10b Richmond ML. Sprout CM. Seto CT. J. Org. Chem. 2005, 70: 8835 11a Wipf P. Xu W. Tetrahedron Lett. 1994, 35: 5197 11b Wipf P. Xu W. Org. Synth. 1996, 74: 205 11c Wipf P. Ribe S. J. Org. Chem. 1998, 63: 6454 12 Schmidt F. Stemmler RT. Rudolph J. Bolm C. Chem. Soc. Rev. 2006, 35: 454 13a Bolm C. Rudolph J. J. Am. Chem. Soc. 2002, 124: 14850 13b Rudolph J. Schmidt F. Bolm C. Synthesis 2005, 840 14a Rudolph J. Hermanns N. Bolm C. J. Org. Chem. 2004, 69: 3997 14b Rudolph J. Lormann M. Bolm C. Dahmen S. Adv. Synth. Catal. 2005, 347: 1361 15 Duan H.-F. Xie J.-H. Shi W.-J. Zhang Q. Zhou Q.-L. Org. Lett. 2006, 8: 1479 16 In these studies, the NMR solvent forms a hydrogen bond to the hydroxy group of the product. The thus formed π-complex (see Figure [2] ) and the additional ring current effect lead to a shift of the NMR signals to higher ppm values.17 NMR spectra were not recorded in CDCl3 due to decomposition of the product. 18 Igushi M. Doi H. Hata S. Tomioka K. Chem. Pharm. Bull. 2004, 52: 125 19 Von Matt P. Lloyd-Jones GC. Minidis ABE. Pfaltz A. Macko L. Neuburger M. Zehnder M. Rüegger H. Pregosin PS. Helv. Chim. Acta 1995, 78: 265 20 Kuroboshi M. Tanaka M. Kishimoto S. Goto K. Mochizuki M. Tanaka H. Tetrahedron Lett. 2000, 41: 81 21 Tajbakhsh M. Lakouraj MM. Shirini F. Habibzadeh S. Nikdoost A. Tetrahedron Lett. 2004, 45: 3295 22 Singh J. Kaur I. Kaur J. Bhalla A. Kad GL. Synth. Commun. 2003, 33: 191
