Reactions of a New Sorensen-type Nucleophile with Organoiron Complexes: Synthesis of N-Deprotected, Diastereomerically Pure Amino Acids

Synlett

Volumn 1996, Issue 9, 1996, Pages 845-846

  Hudson, Richard D A ^a   Osborne, Simon A ^b   Stephenson, G Richard ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345312174     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5609     Document Type: Article

References (22)

1. Dunn M. J.; Jackson R. F. W.; Stephenson G. R.; Synlett. 1992, 905.
2. Genet J, P,; Hudson R. D. A.; Meng W. D.; Roberts E.; Stephenson G. R.; Synlett, 1994, 631.
3. Hudson R. D. A.; Stephenson G. R.; unpublished results.
4. Williams R. M.; Synthesis of Optically Active α-Amino Acids; Pergamon Press, Oxford, England, 1989, Chapter 1 and references therein.
5. Sorenson Z.; Bull. Soc. Chim., 1905, 1042. Sorenson Z.; Bull. Soc. Chim., 1905, 1052; for a recent application of this procedure see Christensen I. T.; Edbert B.; Nielsen B.; Brehm L.; K-Larsen P.; J. Med. Chem., 1992, 35, 3512.
6. Sorenson Z.; Bull. Soc. Chim., 1905, 1042. Sorenson Z.; Bull. Soc. Chim., 1905, 1052; for a recent application of this procedure see Christensen I. T.; Edbert B.; Nielsen B.; Brehm L.; K-Larsen P.; J. Med. Chem., 1992, 35, 3512.
7. Sorenson Z.; Bull. Soc. Chim., 1905, 1042. Sorenson Z.; Bull. Soc. Chim., 1905, 1052; for a recent application of this procedure see Christensen I. T.; Edbert B.; Nielsen B.; Brehm L.; K-Larsen P.; J. Med. Chem., 1992, 35, 3512.
8. Birch A. J.; Cross P. E.; Lewis J.; White D. A.; Wild S. B.; J. Chem. Soc., (A), 1968, 332; Pearson A. J.; J. Chem. Soc., Perkin Trans. 1, 1977, 2069.
9. Birch A. J.; Cross P. E.; Lewis J.; White D. A.; Wild S. B.; J. Chem. Soc., (A), 1968, 332; Pearson A. J.; J. Chem. Soc., Perkin Trans. 1, 1977, 2069.
10. Acidic (HCl, HBr) and basic (NaOH, LiOH) conditions were employed to deprotect 3 but only starting material was recovered or decomposition occurred.
11. Chandler M.; Parsons P. J.; Tetrahedron Lett., 1983, 5781.
12. Sakakura T.; Tanaka M.; J. Chem. Soc., Chem. Commun., 1985, 1309.
13. Khan N. H.; Kidwai A. R.; J. Org. Chem., 1973, 822.
14. Compound 8 was characterised by NMR and IR speciroscopy and was fully characterised as its CBZ derivative.
15. The yields of these reactions were low (<50%), but no other iron-containing compounds (including the other diastereoisomers in cases 10a-c), could be found in the reaction mixtures.
16. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
17. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
18. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
19. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
20. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
21. For examples see: Birch A. J.; Bandara B. M. R.; Tetrahedron Lett., 1980, 21, 2981; Birch A. J.; Raverty W. D.; Stephenson G. R.; Tetrahedron Lett., 1980, 197; Howell J. A. S.; Thomas M. J.; J. Organometal. Chem., 1983, 247; Howell J. A. S.; Thomas M. J.; J. Chem. Soc., Dalton Trans., 1983, 1401. Howard P. W.; Stephenson G. R.; J. Organometal. Chem. 1989, 97. Howard P. W.; Stephenson G. R.; Taylor S. C. J. Chem. Soc., Chem. Commun., 1990, 1182.
22. Howard P. W.; Stephenson G. R.; Taylor S. C.; J. Chem. Soc., Chem. Commun., 1991, 127.