Enantioselective Addition of Dimethylzinc to Aldehydes Catalyzed by a Chiral Perhydro-1,3-benzoxazine-Based Amino Alcohol as Ligand

Abstract

Dimethylzinc undergoes efficient enantioselective addition to a wide variety of aromatic and aliphatic aldehydes in the presence of a catalytic amount of a chiral perhydro-1,3-benzoxazine-based amino alcohol. Methyl carbinols are obtained in good yields and in enantiomeric excesses of 99% or more in the absence of any metal other than zinc.

Key words

asymmetric catalysis - zinc - aldehydes - chiral auxiliaries - amino alcohols

• References

• 1 Soai K, Niwa S. Chem. Rev. 1992; 92: 833
• 2 Noyori R, Kitamura M. Angew. Chem., Int. Ed. Engl. 1991; 30: 49
• 3 Pu L, Yu H.-B. Chem. Rev. 2001; 101: 757
• 4 Soai K, Shibata T In Comprehensive Asymmetric Catalysis . Vol. II. Jacobson EN, Pfaltz A, Yamamoto H. Springer; New York: 1999. Chap. 26, 911
• 5a Robin S, Huet F, Fauve A, Vescambre H. Tetrahedron: Asymmetry 1993; 4: 239
• 5b Jones GB, Heaton SB. Tetrahedron: Asymmetry 1993; 4: 261
• 5c Jones GB, Guzel M, Chapman BJ. Tetrahedron: Asymmetry 1998; 9: 901
• 5d Jones GB, Huber RS, Chapman BJ. Tetrahedron: Asymmetry 1997; 8: 1797
• 5e Scott MS, Luckhurst CA, Dixon DJ. Org. Lett. 2005; 7: 5813
• 5f Sabitha G, Reddy CS, Yadav JS. Tetrahedron Lett. 2006; 47: 4513
• 6 Kitamura M, Okada S, Suga S, Noyori R. J. Am. Chem. Soc. 1989; 111: 4028
• 7 Cozzi PG, Kotrusz P. J. Am. Chem. Soc. 2006; 128: 4940
• 8 Blay G, Fernández I, Hernández-Olmos V, Marco-Aleixandre A, Pedro JR. Tetrahedron: Asymmetry 2005; 16: 1953
• 9 Sokeirik YS, Mori H, Omote M, Sato K, Tarui A, Kumadaki I, Ando A. Org. Lett. 2007; 9: 1927
• 10 Muñiz K. Tetrahedron Lett. 2003; 44: 3547
• 11a Dangel BD, Polt R. Org. Lett. 2000; 2: 3003
• 11b Hatano M, Miyamoto T, Ishihara K. J. Org. Chem. 2006; 71: 6474
• 12 Wolf C, Liu S. Org. Lett. 2007; 9: 2965
• 13 Wang M.-C, Zhang Q.-J, Zhao W.-X, Wang X.-D, Ding X, Jing T.-T, Song M.-P. J. Org. Chem. 2008; 73: 168
• 14 Rodríguez-Escrich S, Reddy KS, Jimeno C, Colet G, Rodríguez-Escrich C, Solà L, Vidal-Ferran A, Pericàs MA. J. Org. Chem. 2008; 73: 5340
• 15a Wang M.-C, Zhang Q.-J, Li G.-W, Liu Z.-K. Tetrahedron: Asymmetry 2009; 20: 288
• 15b Binder CM, Bautista A, Zaidlewicz M, Krzemiński MP, Oliver A, Singaram B. J. Org. Chem. 2009; 74: 2337
• 15c Leven M, Schlörer NE, Neudörfl JM, Goldfuss B. Chem.–Eur. J. 2010; 16: 13443
• 16a Andrés C, Infante R, Nieto J. Tetrahedron: Asymmetry 2010; 21: 2230
• 16b Infante R, Nieto J, Andrés C. Org. Biomol. Chem. 2011; 9: 6691
• 17a Yamakawa M, Noyori R. J. Am. Chem. Soc. 1995; 117: 6327
• 17b Yamakawa M, Noyori R. Organometallics 1999; 18: 128
• 18 Pedrosa R, Andrés C, Rosón CD, Vicente M. J. Org. Chem. 2003; 68: 1852
• 19 Andrés C, González I, Nieto J, Rosón CD. Tetrahedron 2009; 65: 9728
• 20 Xiao J, Wong ZZ, Lu YP, Loh TP. Adv. Synth. Catal. 2010; 352: 1107
• 21 Li DR, He A, Falck JR. Org. Lett. 2010; 12: 1756
• 22 Xu Y, Alcock NW, Clarkson GJ, Docherty G, Woodward G, Wills M. Org. Lett. 2004; 6: 4105
• 23 Inagaki T, Phong LT, Furuta A, Ito J.-I, Nishiyama H. Chem.–Eur. J. 2010; 16: 3090
• 24 Inagaki T, Ito A, Ito J.-I, Nishiyama H. Angew. Chem. Int. Ed. 2010; 49: 9384
• 25 Junge K, Wendt B, Addis D, Zhou S, Das S, Fleischer S, Beller M. Chem.–Eur. J. 2011; 17: 101
• 26 Kantam ML, Yadav J, Laha S, Srinivas P, Sreedhar B, Figueras F. J. Org. Chem. 2009; 74: 4608
• 27 Nolin KA, Ahn RW, Kobayashi Y, Kennedy-Smith JJ, Toste FD. Chem.–Eur. J. 2010; 16: 9555
• 28 Evans EA, Anderson JC, Taylor MK. Tetrahedron Lett. 1993; 34: 5563
• 29 Hagiya K, Muramoto N, Misaki T, Sugimura T. Tetrahedron 2009; 65: 6109
• 30a Ghosh AK, Bilcer G, Schiltz G. Synthesis 2001; 2203
• 30b List B, Castello C. Synlett 2001; 1687
• 31 Irgolic KJ In Methoden der Organischen Chemie (Houben–Weyl). Vol. E12b. Klamann D. Thieme; Stuttgart: 1990: 150