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Synthesis 2014; 46(13): 1765-1772
DOI: 10.1055/s-0033-1341226
DOI: 10.1055/s-0033-1341226
paper
One-Pot Parallel Synthesis Approach to Secondary Amines Based on the Reductive Amination of Ketones
Further Information
Publication History
Received: 05 February 2014
Accepted after revision: 21 March 2014
Publication Date:
11 April 2014 (online)
Abstract
A combination of a condensation mixture [a Lewis acid, Ti(Oi-Pr)4, and a water scavenger, 1-(trimethylsilyl)-2-pyrrolidinone] and a simple reductant (NaBH4) provides an efficient one-pot approach to parallel synthesis of secondary amines by the reductive amination of ketones. The approach demonstrated its applicability to a variety of substrates with different degree of hindrance of an amino or a carbonyl group affording products in moderate to high yields.
Key words
combinatorial chemistry - one-pot approach - parallel synthesis - reductive amination - secondary aminesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Tarasevich VA, Kozlov NG. Russ. Chem. Rev. 1999; 68: 55
- 2 Abdel-Magid AF, Mehrman SJ. Org. Process Res. Dev. 2006; 10: 971
- 3 Tripathi RP, Verma SS, Pandey J, Tiwari VK. Curr. Org. Chem. 2008; 12: 1093
- 4 Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
- 5 Salvatore RN, Yoon CH, Jung KW. Tetrahedron 2001; 57: 7785
- 6 Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. Nucleic Acids Res. 2012; 40: D1100
- 7 Borch RF, Bernstein MD, Durst HD. J. Am. Chem. Soc. 1971; 93: 2897
- 8 McGonagle FI, MacMillan DS, Murray J, Sneddon HF, Jamieson C, Watson AJ. B. Green Chem. 2013; 15: 1159
- 9 Abdel-Magid AF, Maryanoff CA, Carson KG. Tetrahedron Lett. 1990; 31: 5595
- 10 Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. J. Org. Chem. 1996; 61: 3849
- 11 Alinezhad H, Tajbakhsh M, Zamani R. Synlett 2006; 431
- 12 Bhattacharyya S, Chatterjee A, Duttachowdhury SK. J. Chem. Soc., Perkin Trans. 1 1994; 1
- 13 Zhang W, Zhang X In Comprehensive Chirality . Vol. 5. Carreira EM, Yamamoto H. Elsevier; Amsterdam: 2012: 301-317
- 14 Mićović IV, Ivanović MD, Piatak DM, Bojić VD. Synthesis 1991; 1043
- 15 Hiroi R, Miyoshi N, Wada M. Chem. Lett. 2002; 31: 274
- 16 Apodaca R, Xiao W. Org. Lett. 2001; 3: 1745
- 17 Lee O.-Y, Law K.-L, Ho C.-Y, Yang D. J. Org. Chem. 2008; 73: 8829
- 18 Bomann MD, Guch IC, DiMare M. J. Org. Chem. 1995; 60: 5995
- 19 Sato S, Sakamoto T, Miyazawa E, Kikugawa Y. Tetrahedron 2004; 60: 7899
- 20 Neidigh KA, Avery MA, Williamson JS, Bhattacharyya S. J. Chem. Soc., Perkin Trans. 1 1998; 2527
- 21 Kumpaty HJ, Williamson JS, Bhattacharyya S. Synth. Commun. 2003; 33: 1411
- 22 Ryabukhin SV, Panov DM, Plaskon AS, Chuprina A, Pipko SE, Tolmachev AA, Shivanyuk AN. Mol. Divers. 2012; 16: 625
- 23 Hua DH, Miao SW, Bharathi SN, Katsuhira T, Bravo AA. J. Org. Chem. 1990; 55: 3682