Palladium(0) catalysed rearrangements of allylic sulfoximines to allyl sulfinimidic acid esters and optically active N-Cbz protected γ-amino- enomes

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8499-8502

  Pyne, Stephen G ^a   David, Dorothy M ^a   Dong, Zemin ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

Asymmetric synthesis; Palladium and compounds; Rearrangements; Sulfoximines

Indexed keywords

ESTER; IMINE; KETONE; LIGAND; PALLADIUM; SULFOXIMINE; UNCLASSIFIED DRUG;

CATALYSIS; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; REVIEW; SYNTHESIS;

EID: 0032511949     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01847-4     Document Type: Article

References (12)

1. [1] David, D. M.; O'Meara, G. W.; Pyne, S. G. Tetrahedron Lett.; 1996; 37: 5417.
2. [2] Pyne, S. G.; O'Meara, G. W.; David, D. M. Tetrahedron Lett.; 1997; 38: 3623.
3. [3] For other procedures for preparing these compounds in optically active form see: Ikota, N. Heterocycles; 1995; 41: 983. Wei, Z. Y.; Knaus, E. E. Org. Prep. & Proc. Int; 1994; 26: 243. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc; 1995; 117: 1225. Reetz, M. T.; Rohrig, D. Angew. Chem., Int. Ed. Engl.; 1989; 28: 1706. Enders, D.; Bettray, W. Pure Appl. Chem.; 1996; 68: 569.
4. [3] For other procedures for preparing these compounds in optically active form see: Ikota, N. Heterocycles; 1995; 41: 983. Wei, Z. Y.; Knaus, E. E. Org. Prep. & Proc. Int; 1994; 26: 243. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc; 1995; 117: 1225. Reetz, M. T.; Rohrig, D. Angew. Chem., Int. Ed. Engl.; 1989; 28: 1706. Enders, D.; Bettray, W. Pure Appl. Chem.; 1996; 68: 569.
5. [3] For other procedures for preparing these compounds in optically active form see: Ikota, N. Heterocycles; 1995; 41: 983. Wei, Z. Y.; Knaus, E. E. Org. Prep. & Proc. Int; 1994; 26: 243. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc; 1995; 117: 1225. Reetz, M. T.; Rohrig, D. Angew. Chem., Int. Ed. Engl.; 1989; 28: 1706. Enders, D.; Bettray, W. Pure Appl. Chem.; 1996; 68: 569.
6. [3] For other procedures for preparing these compounds in optically active form see: Ikota, N. Heterocycles; 1995; 41: 983. Wei, Z. Y.; Knaus, E. E. Org. Prep. & Proc. Int; 1994; 26: 243. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc; 1995; 117: 1225. Reetz, M. T.; Rohrig, D. Angew. Chem., Int. Ed. Engl.; 1989; 28: 1706. Enders, D.; Bettray, W. Pure Appl. Chem.; 1996; 68: 569.
7. [3] For other procedures for preparing these compounds in optically active form see: Ikota, N. Heterocycles; 1995; 41: 983. Wei, Z. Y.; Knaus, E. E. Org. Prep. & Proc. Int; 1994; 26: 243. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc; 1995; 117: 1225. Reetz, M. T.; Rohrig, D. Angew. Chem., Int. Ed. Engl.; 1989; 28: 1706. Enders, D.; Bettray, W. Pure Appl. Chem.; 1996; 68: 569.
8. [4] von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed.; 1993; 32: 566. Sprinz, J.; Helmchen, G. Tetrahedron Lett.; 1993; 34: 1769. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett.; 1993; 34: 2015.
9. [4] von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed.; 1993; 32: 566. Sprinz, J.; Helmchen, G. Tetrahedron Lett.; 1993; 34: 1769. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett.; 1993; 34: 2015.
10. [4] von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed.; 1993; 32: 566. Sprinz, J.; Helmchen, G. Tetrahedron Lett.; 1993; 34: 1769. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett.; 1993; 34: 2015.
11. [5] Gais, H.-J. Scommoda, M., Lenz, D. Tetrahedron Lett.; 1994; 35: 7361.
12. [6] For related procedures see: Haynes, R. K.; Vonwiller, S. C.; Stokes, J. P.; Merlino, L. M. Aust. J. Chem.; 1988; 41: 881.