Enantiospecific synthesis of isomers of AES, a new environmentally friendly chelating agent

Tetrahedron

Volumn 60, Issue 48, 2004, Pages 10949-10954

  Pihko, Petri M ^a   Rissa, Terhi K ^a   Aksela, Reijo ^b  

^a AALTO UNIVERSITY   (Finland)

^b KEMIRA OYJ   (Finland)

Author keywords

Aldehydes; Amino acids; Chelating agents; Reductive amination; Stereoisomerism

Indexed keywords

ASPARTIC ACID; CHELATING AGENT; MALIC ACID;

ARTICLE; BIODEGRADABILITY; DIASTEREOISOMER; ISOMER; PRIORITY JOURNAL; STEREOISOMERISM; SYNTHESIS;

EID: 14344264274     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.024     Document Type: Article

References (12)

1. D. Williams Chem. Ber. 34 1998 48
2. J.R. Hart Ethylenediacetic Acid and Related Chelating Agents Ullmann's Encyclopedia of Industrial Chemistry 7th ed. 2003 Wiley-VCH Weinheim Release 2003
3. J.L. Means, T. Kucak, and D.A. Crerar Environ. Pollut. (Ser B) 1 1980 45
4. For further examples, see: S. Metsärinne, P. Rantanen, R. Aksela, and T. Tuhkanen Chemosphere 55 2004 379 and references therein
5. J.A. Neal, and N.J. Rose Inorg. Chem. 7 1968 2405 and references therein
6. (a) Aksela, R.; Renvall, I.; Paren, A. PCT Int. Appl. WO 9745396;
7. (b) Aksela, R.; Renvall, I.; Paren, A. PCT Int. Appl. WO 9946234.
8. Itävaara, M.; Vikman, M. Research Report No BEL 235/97; Technical Research Centre of Finland: Espoo, Finland.
9. See Ref. 5b. For earlier examples of similar reactions, see: J. van Westrenen, R.M. Roggen, M.A. Hoefnagel, A.J. Peters, A.P.G. Kieboom, and H. Bekkum Tetrahedron 46 1990 5741
10. The (S,S) isomer of EDDS is completely biodegradable, while the enantiomeric (R,R) isomer is only marginally degraded in the standard Sturm test. See: D. Schowanek, T.C.J. Feijtel, C.M. Perkins, F.A. Hartman, T.W. Federle, and R.J. Larson Chemosphere 34 1997 2375
11. For a recent review of reductive aminations with borohydrides, see: E.W. Baxter, and A.B. Reitz Reductive aminations of carbonyl compounds with borohydride and borane reducing agents Org. React. (N.Y.) 59 2002 1
12. A. Dahlgren, P.-O. Johansson, I. Kvarnström, D. Musil, I. Nilsson, and B. Samuelsson Bioorg. Med. Chem. Lett. 10 2002 1829