Dutch Resolution: Separation of Enantiomers with Families of Resolving Agents. A Status Report

Abstract

Dutch Resolution is the term given to the use of mixtures (families) of resolving agents in classical resolutions. In this status report an overview is given of the latest results and new (possible) families of resolving agents are introduced. The concept of families is discussed as well as the factors that come into play on use of families. Practical aspects of Dutch Resolution in particular and resolutions in general are discussed.

Key words

amino alcohols - asymmetric synthesis - chiral auxil­iaries - chiral resolution - chirality - camphor - chalcones - sulfonic acids

References

• 1a Rouhi M. Chem. Eng. News  2002,  80(23):  43 
• 2a Sheldon RA. Chirotechnology   Chap. 6:  Marcel Dekker; New York: 1993. 
• 2b Chirality in Industry II   Collins NA. Sheldrake GN. Crosby J. Wiley; Chichester: 1997. 
• 3a Vries T. Wynberg H. van Echten E. Koek J. ten Hoeve W. Kellogg RM. Broxterman QB. Minnaard A. Kaptein B. van der Sluis S. Hulshof LA. Kooistra J. Angew. Chem. Int. Ed.  1998,  37:  2349 
• 3b See also: Broxterman QB. van Echten E. Hulshof LA. Kaptein B. Kellogg RM. Minnaard AJ. Vries TR. Wynberg H. Chem. Today  1998,  129:  4278 
• 4 Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions   Wiley; New York: 1981. 
• 5a For a broad overview see: Noyori R. Angew. Chem. Int. Ed.  2002,  41:  2008 
• Excellent books and chapters on resolution phenomena are:
• 6a Kozma D. Handbook of Optical Resolutions via Diastereomeric Salt Formation   CRC Press; Boca Raton: 2002. 
• 6b Eliel EL. Wilen SH. Stereochemistry of Organic Compounds   Chap. 7:  Wiley-Interscience; New York: 1994. 
• 6c

  See also 2a

• 6d Wilen SH. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry   Wiley-Interscience; New York: 1971.  Vol. 6.
• 6e Wilen SH. Tables of Resolving Agents and Optical   Eliel EL. University of Notre Dame Press; London: 1972. 
• 6f Newman P. Optical Resolutions Procedures for Chemical Compounds   Optical Resolution Information Centre; New York: 1971. 
• 7a ten Hoeve W. Wynberg H. J. Org. Chem.  1985,  50:  4508 
• 7b ten Hoeve W, and Wynberg H. inventors; Eur. Pat. 180,276 1989; US Pat.  4,814,477. 
• 8 Gizur T. Péteri I. Harsányi K. Fogassy E. Tetrahedron: Asymmetry  1996,  7:  1589 
• 9 Nieuwenhuijzen JW. Grimbergen RFP. Koopman C. Kellogg RM. Vries TR. Pouwer K. van Echten E. Kaptein B. Hulshof LA. Broxterman QB. Angew. Chem. Int. Ed.  2002,  41:  4281 
• 10a Bouillon D, Vayssie C, and Richard F. inventors; US Patent  4,304,730. 
• 10b Bouillon D, Vayssie C, and Richard F. inventors; US Patent  4,330488. 
• 10c inventors; Bouillon C., Vayssie C., Richard F. US Patent  4,323,549.  ; and further patents cited; for some other sulfonic acid derivatives see:
• 10d Boesten WHJ. inventors; US Patent  4,111,980. 
• 10e Bruggink A. Roos EC. De Vroom E. Org. Process Res. Dev.  1998,  2:  128 
• 11a Evans EB. Mabbott EE. Turner EE. J. Chem. Soc.  1927,  1159 
• 11b Anderson AR. Short WF. J. Chem. Soc.  1933,  485 
• 11c Agami C. Prince B. Puchot C. Synth. Commun.  1990,  20:  3289 
• 11d Ashworth F. Burkhardt GN. J. Chem. Soc.  1928,  1791 
• 11e for a review on sulfonations see: Gilbert EE. Synthesis  1969,  1:  3 
• 12a Corey EJ. Cimprich KA. Tetrahedron Lett.  1992,  33:  4099 
• 12b Corey EJ. Bakshi RK. Shibata S. J. Am. Chem. Soc.  1987,  109:  5551 
• 12c Corey EJ. Shibata S. Bakshi RK. J. Org. Chem.  1988,  53:  2861 
• 12d Corey EJ. Bakshi RK. Tetrahedron Lett.  1990,  31:  611 
• 13a Yoshioka R. Tohyama M. Ohtsuki O. Yamada S. Chibata I. Bull. Chem. Soc. Jpn.  1987,  60:  649 
• 13b Yoshioka R. Ohtsuki O. Senuma M. Tosa T. Chem. Pharm. Bull.  1989,  37:  883 
• 13c Yoshioka R. Ohtsuki O. Da-Te T. Okamura K. Senuma M. Bull. Chem. Soc. Jpn.  1994,  67:  3012 
• 13d Yoshioka R. Okamura K. Yamada S. Aoe K. Da-Te T. Bull. Chem. Soc. Jpn.  1998,  71:  1109 
• 14 Knoevenagel E. Berichte  1904,  31:  4038 
• 15 Pfoertner KH. Helv. Chim. Acta  1980,  63:  664 
• 16a Dahlman O. Månson K. J. Wood Chem. Technol.  1996,  16:  47 
• 16b Richtzenhain H. Alfredsson B. Berichte  1956,  89:  378 
• 16c Richtzenhain H. Berichte  1939,  72:  2152 
• 16d Kratzl K. Däubner H. Monatsh. Chem.  1948,  78:  376 
• 16e Browne MF. Shriner RL. J. Org. Chem.  1957,  22:  1320 
• 16f Kratzl D. Däubner H. Berichte  1944/1946,  77/79:  519 
• 17a Chirality in Industry II   Collins NA. Sheldrake GN. Crosby J. Wiley; Chichester: 1997.  p.101 
• 17b Watanabe M. Murata K. Ikariya T. J. Org. Chem.  2002,  67:  1712 
• 18 Van der Sluis M. Dalmolen J. de Lange B. Kaptein B. Kellogg RM. Broxterman QB. Org. Lett.  2001,  3:  3943 
• 20 Fogassy E. Lopata A. Faigl F. Darvas F. Ács M. Toke L. Tetrahedron Lett.  1980,  21:  647 
• 21 Pope WJ. Peachy SJ. J. Chem. Soc.  1899,  5:  1066 
• 23 Kohler EP. Chadwell HM. Org. Synth., Coll. Vol. I   Wiley; New York: 1941.  p.78 
• 24 López SN. Castelli MV. Azcchino SA. Domínguez JN. Lobo G. Charris-Charris J. Cortés JCG. Ribas JC. Devia C. Rodríguez AM. Enriz RD. Bioorg. Med. Chem.  2001,  9:  1999 
• 25 Silver NL. Boykin DW. J. Org. Chem.  1970,  35:  759 

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Dalmolen, J. Eur. J. Org. Chem. to be submitted .

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Kaptein, B. et al. manuscript in preparation.

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