A Magnesium-Based Diastereoselective Preparation of Pyridylic 1,3-Amino Alcohols Using the tert-Butyl Sulfinamide Auxiliary

Abstract

1,3-Amino alcohols were prepared by using a two-step approach and an interesting reversal in diastereoselectivity is discussed.

Key words

organometallic addition - diastereoselectivity - sulfinamides - halogen-metal exchange - amino alcohol

• References

• 1 Barrow JC, Bieber K.-AS, Cube RV, Mattern MC, Reger TS, Shu Y, Yang Z.-Q. WO 2007120729, 2007 ; Chem. Abstr. 2007, 147, 486333.
• 2 Xie Y, Guo P. CN 101875666, 2010
• 3 Villadsen JS, Stephansen HM, Maolanon AR, Harris P, Olsen CA. J. Med. Chem. 2013; 56: 6512
• 4 Liu G, Cogan DA, Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913
• 5 Barrow JC, Ngo PL, Pellicore JM, Selnick HG, Nantermet PG. Tetrahedron Lett. 2001; 42: 2051
• 6 Chen BL, Wang B, Lin GQ. J. Org. Chem. 2009; 75: 941
• 7 Cogan DA, Liu G, Ellman J. Tetrahedron 1999; 55: 8883
• 8 Dema HK, Foubelo F, Yus M. Helv. Chim. Acta 2012; 95: 1790
• 9 Evans JW, Ellman JA. J. Org. Chem. 2003; 68: 9948
• 10 Kuduk SD, DiPardo RM, Chang RK, Ng C, Bock MG. Tetrahedron Lett. 2004; 45: 6641
• 11 Tang TP, Ellman JA. J. Org. Chem. 2002; 67: 7819
• 12 Chen Y, Goldberg FW, Xiong J, Wang S. Synthesis 2015; 47: 679
• 13 Tang TP, Volkman SK, Ellman JA. J. Org. Chem. 2001; 66: 8772
• 14 Tanaka K, Shiraishi S, Nakai T, Ishikawa N. Tetrahedron Lett. 1978; 3103
• 15 Donner CD. Org. Lett. 2013; 15: 1258
• 16 Wang J, Chen J, Kee CW, Tan CH. Angew. Chem. Int. Ed. 2012; 51: 2382
• 17 Krasovskiy A, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333
• 18 Ren H, Krasovskiy A, Knochel P. Org. Lett. 2004; 6: 4215
• 19 Kadam A, Nguyen M, Kopach M, Richardson P, Gallou F, Wan ZK, Zhang W. Green Chem. 2013; 15: 1880
• 20 Aycock DF. Org. Process Res. Dev. 2006; 11: 156
• 21 Bauer RA, DiBlasi CM, Tan DS. Org. Lett. 2010; 12: 2084
• 22 Davis FA, McCoull W. J. Org. Chem. 1999; 64: 3396
• 23 Eskildsen J, Redrobe JP, Sams AG, Dekermendjian K, Laursen M, Boll JB, Papke RL, Bundgaard C, Frederiksen K, Bastlund JF. Bioorg. Med. Chem. Lett. 2014; 24: 288
• 24 Aggarwal VK, Barbero N, McGarrigle EM, Mickle G, Navas R, Suárez JR, Unthank MG, Yar M. Tetrahedron Lett. 2009; 50: 3482
• 25 Wakayama M, Ellman JA. J. Org. Chem. 2009; 74: 2646
• 26 Solladié G. Synthesis 1981; 185
• 27 Mikolajczyk M, Drabowicz J. Synthesis 1974; 124
• 28 Drabowicz J, Legedz S, Mikolajczyk M. Tetrahedron 1988; 44: 5243
• 29 Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 14844
• 30 Budavari S. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. Merck; Rahway (NJ, USA): 1989
• 31 Nara SJ, Jha M, Brinkhorst J, Zemanek TJ, Pratt DA. J. Org. Chem. 2008; 73: 9326
• 32 Raghavan S, Krishnaiah V. J. Org. Chem. 2009; 75: 748
• 33 Yamamoto Y, Kurihara K, Miyaura N. Angew. Chem. Int. Ed. 2009; 48: 4414