Highly diastereoselective alkylation of the Dellaria oxazinone template with bifunctional electrophiles

Synthetic Communications

Volumn 33, Issue 13, 2003, Pages 2197-2208

  Roos, Gregory H P ^a   Dastlik, Kim A ^b  

^a SULTAN QABOOS UNIVERSITY   (Oman)

^b MURDOCH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; KETONE DERIVATIVE; OXAZINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037677152     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021497     Document Type: Article

References (13)

1. For recent general compilations see (a) Roos, G.H.P. Alkylation and related reactions. Compendium of Chiral Auxiliary Applications; Academic Press: London, 2002; Vol. 1, 218; (b) Seyden-Penne, J. Alkylation and related reactions. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley-Interscience: New York, 1995; 157.
2. For recent general compilations see (a) Roos, G.H.P. Alkylation and related reactions. Compendium of Chiral Auxiliary Applications; Academic Press: London, 2002; Vol. 1, 218; (b) Seyden-Penne, J. Alkylation and related reactions. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley-Interscience: New York, 1995; 157.
3. (a) Williams, R.M. Synthesis of Optically Active α-Amino Acids; Baldwin, J.E., Magnus, P.D., Eds.; Pergamon Press: Oxford, 1989; Vol. 7;
4. (b) Seebach, D.; Sting, A.R.; Hoffman, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708.
5. (a) Dellaria, J.F.; Santarsiero, B.D. Tetrahedron Lett. 1988, 29, 6079;
6. (b) Dellaria, J.F.; Santarsiero, B.D. J. Org. Chem. 1989, 54, 3916.
7. Dastlik, K.A.; Roos, G.H.P.; Giles, R.G.F. Tetrahedron: Asymmetry 1996, 7, 2525.
8. Whilst reaction monitoring indicated a single major product, extensive decomposition prevented further characterization.
9. Uenishi, J.; Tatsumi, Y.; Kobayashi, N.; Yonemitsu, O. Tetrahedron Lett. 1995, 36, 5909.
10. Baldwin, J.E.; Spivey, A.C.; Schofield, C.J.; Sweeney, J.B. Tetrahedron 1993, 49, 6309.
11. Hockless, D.C.R.; Mayadunne, R.C,; Wild, S.B. Tetrahedron: Asymmetry 1995, 6, 3031.
12. For the general approach to the haloalcohols, see: Shea, K.J.; Burke, L.D. J. Org. Chem. 1988, 53, 318.
13. Xu, Y.-C.; Wulff, W.D. J. Org. Chem. 1987, 52, 3263.