Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: A pyrrolidine-derived arylglycine synthesis

Tetrahedron Letters

Volumn 46, Issue 12, 2005, Pages 2025-2028

  Nanda, Kausik K ^a   Trotter, B Wesley ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Arylglycine; Boronic acid Mannich; Diastereoselective; Petasis

Indexed keywords

AMINE; BORONIC ACID DERIVATIVE; GLYCINE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; HEXAFLUORO 2 PROPANOL; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; MANNICH REACTION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 14644412877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.151     Document Type: Article

References (21)

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2. N.A. Petasis, and I.A. Zavialov J. Am. Chem. Soc. 119 1997 445
3. N.A. Petasis, and I.A. Zavialov J. Am. Chem. Soc. 120 1998 11798
4. N.A. Petasis, A. Goodman, and I.A. Zavialov Tetrahedron 53 1997 16463
5. Arylglycine epimerization is well documented in the literature: C. Mellin-Morliere, D.J. Aitken, S.D. Bull, S.G. Davies, and H.H. Husson Tetrahedron: Asymmetry 12 2001 149
6. R.M. Williams Synthesis of Optically Active α-Amino Acids 1989 Pergamon Oxford
7. Harwood and co-workers have reported a related diastereoselective reaction of 2-furyl boronic acid and formaldehyde in a non-epimerizable system: G.S. Currie, M.G.B. Drew, L.M. Harwood, D.J. Hughes, R.W.A. Luke, and R.J. Vickers J. Chem. Soc., Perkin Trans. 1 2000 2982
8. N.A. Petasis, and Z.D. Patel Tetrahedron Lett. 41 2000 9607
9. Amino acids obtained from the boronic acid Mannich reactions were converted into the corresponding methyl esters (TMSCHN2) for ease of purification and characterization
10. HFIP has been found to accelerate substitution reactions of dihydroartemisinin derivatives. Bonnet-Delpon and co-workers speculated that this is due to the strong hydrogen bond donor ability of HFIP: G. Magueur, B. Crousse, M. Ourevitch, J.P. Begue, and D. Bonnet-Delpon J. Org. Chem. 68 2003 9763
11. For other HFIP-accelerated reactions see: J. Iskra, D. Bonnet-Delpon, and J.P. Begue Eur. J. Org. Chem. 2002 3402
12. J. Ichikawa, S. Miyazaki, M. Fujiwara, and T. Minami J. Org. Chem. 60 1995 2320
13. R. Takita, T. Ohshima, and M. Shibasaki Tetrahedron Lett. 43 2002 4661
14. 2 at room temperature provided 61% conversion by LC/MS after 26 h
15. V. Frenna, and N. Vivona J. Chem. Soc., Perkin Trans. 2 1985 1865
16. S. Searles, M. Tamres, F. Block, and L.A. Quarterman J. Am. Chem. Soc. 78 1956 4917
17. 2-HFIP, 0°C, 5.5 h, 94% conversion, 92% yield, diastereomeric ratio 69:31
18. Reactivities of several other acyclic and cyclic amines were examined. In general, acyclic amines showed no reaction or very little conversion to the desired arylglycines. See Table S1 in the supporting information
19. 1H NMR spectra of the isolated methyl esters
20. Crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 254668. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ]
21. 11B NMR data: N. Schlienger, M.R. Bryce, and T.K. Hansen Tetrahedron 56 2000 10023