Stereoselective addition of phenyl selenyl chloride to methoxy alkenes derived from N-protected chiral α-amino acids

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4417-4420

  Demarcus, Mariangela ^a   Filigheddu, Silvia N ^a   Mann, André ^b   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

^b CNRS   (France)

Author keywords

Acetals; Chelation; Selenium halogen compounds; Selenonium ions

Indexed keywords

ALPHA AMINO ACID; AZIRIDINE DERIVATIVE; CYSTEINE PROTEINASE INHIBITOR; LITHIUM CHLORIDE; PHENYLSELENYL CHLORIDE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; BIOTRANSFORMATION; CHELATION; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033522959     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00761-3     Document Type: Article

References (12)

1. See for example: Summers, J.B.; Davidsen, S.K. in: Ann. Rep. in Med. Chem., J.A. Bristol Ed., Academic Press, New York, 1998, 131 and references therein.
2. Mann, A.; Quaranta, L.; Reginato, G.; Taddei, M. Tetrahedron Lett. 1996, 37, 2651
3. The results of the inhibition of papaine with peptidomimetics containing an oxirane ring will be reported elsewhere.
4. For a discussion of the stereochemical stability of related sulfenyl aldehydes see: Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165.
5. 3 the starting material is recovered unchanged.
6. The evaluation of the coupling constant was carried out under decoupling of the protons of the R groups.
7. Another possible explanation of the observed increase in stereoselectivity obtained after Lewis acid complexation is a minimisation of the allylic strain.
8. 3) δ 17.6, 28.6, 70.2, 99.6, 145.7, 153.4, 170.2.
9. Filigheddu, S.N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3857. Ziegler, F.E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Funaki, I.; Thijs, L.; Zwanenburg, B. Tetrahedron 1996, 52, 9909. Schirmeister, T. J. Med. Chem. 1999, 42, 560.
10. Filigheddu, S.N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3857. Ziegler, F.E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Funaki, I.; Thijs, L.; Zwanenburg, B. Tetrahedron 1996, 52, 9909. Schirmeister, T. J. Med. Chem. 1999, 42, 560.
11. Filigheddu, S.N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3857. Ziegler, F.E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Funaki, I.; Thijs, L.; Zwanenburg, B. Tetrahedron 1996, 52, 9909. Schirmeister, T. J. Med. Chem. 1999, 42, 560.
12. Filigheddu, S.N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3857. Ziegler, F.E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Funaki, I.; Thijs, L.; Zwanenburg, B. Tetrahedron 1996, 52, 9909. Schirmeister, T. J. Med. Chem. 1999, 42, 560.