A simple circular dichroism method for the determination of the absolute configuration of allylic amines

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2975-2977

  Skowronek, P ^a   Gawronski J ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Amines; Circular dichroism; Configuration

Indexed keywords

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0343238844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00285-9     Document Type: Article

References (20)

1. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
2. (b) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99.
3. (c) Trost, B. M.; Lemoine, R. C. Tetrahedron Lett. 1996, 37, 9161.
4. (d) Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520.
5. Deardorff, D. R.; Linde, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759.
6. Funk, G.; Mulzer, J. Synthesis 1995, 101.
7. Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4202.
8. (a) Kazmierczak, F.; Gawrońska, K.; Rychlewska, U.; Gawroński, J. Tetrahedron: Asymmetry 1994, 5, 527.
9. (b) Gawroński, J.; Kazmierczak, F.; Gawrońska, K.; Rychlewska, U.; Nordén, B.; Holmén, A. J. Am. Chem. Soc. 1998, 120, 12083.
10. For general references, see: (a) Harada, N.; Nakanishi, K. Circular Dichroism Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, 1983.
11. (b) Rodger, A.; Nordén, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, 1997.
12. Molecular modeling was initially performed with the MMX force field (PCMODEL, Serena Software, Bloomington, IN) and complemented by semiempirical calculations of heats of formation with AM1 (HyperChem, HyperCube Inc.).
13. D values of analogous cyclic allylic benzoates, see: Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961.
14. Compounds 4-11 were prepared from (R)-2-amino-1-butanol (ee 80%) or the corresponding L-aminoacid precursors in the sequence of reactions involving reduction to α-aminoalcohols (Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517), followed by N-phthaloylation (Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem 1978, 43, 893), oxidation to α-phthalimidoaldehydes with TEMPO (Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051), and Wittig olefination at -78°C (Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487). The intermediate α-phthalimidoaldehydes showed little racemization (ee>90%), estimated by HPLC on a chiral column (DAICEL OD-H 250/4).
15. Compounds 4-11 were prepared from (R)-2-amino-1-butanol (ee 80%) or the corresponding L-aminoacid precursors in the sequence of reactions involving reduction to α-aminoalcohols (Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517), followed by N-phthaloylation (Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem 1978, 43, 893), oxidation to α-phthalimidoaldehydes with TEMPO (Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051), and Wittig olefination at -78°C (Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487). The intermediate α-phthalimidoaldehydes showed little racemization (ee>90%), estimated by HPLC on a chiral column (DAICEL OD-H 250/4).
16. Compounds 4-11 were prepared from (R)-2-amino-1-butanol (ee 80%) or the corresponding L-aminoacid precursors in the sequence of reactions involving reduction to α-aminoalcohols (Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517), followed by N-phthaloylation (Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem 1978, 43, 893), oxidation to α-phthalimidoaldehydes with TEMPO (Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051), and Wittig olefination at -78°C (Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487). The intermediate α-phthalimidoaldehydes showed little racemization (ee>90%), estimated by HPLC on a chiral column (DAICEL OD-H 250/4).
17. Compounds 4-11 were prepared from (R)-2-amino-1-butanol (ee 80%) or the corresponding L-aminoacid precursors in the sequence of reactions involving reduction to α-aminoalcohols (Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517), followed by N-phthaloylation (Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem 1978, 43, 893), oxidation to α-phthalimidoaldehydes with TEMPO (Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051), and Wittig olefination at -78°C (Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487). The intermediate α-phthalimidoaldehydes showed little racemization (ee>90%), estimated by HPLC on a chiral column (DAICEL OD-H 250/4).
18. H,H in the range 6.6-9.8 Hz between the protons located at the chiral and the olefinic carbon atoms.
19. (a) Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H. J. Am. Chem. Soc. 1981, 103, 5590.
20. (b) Gonnella, N. C.; Nakanishi, K.; Martin, V. S.; Sharpless, K. B. J. Am. Chem. Soc. 1982, 104, 3775.