Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries

Synthetic Communications

Volumn 34, Issue 14, 2004, Pages 2641-2653

  Zaidi, Javid H ^a   Naeem, Fazal ^a   Khan, Khalid M ^b   Iqbal, Rasfaid ^a   Zia Ullah, ^b  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Chiral auxiliaries; Dithioacetals; Oxathioacetals

Indexed keywords

ACETAL DERIVATIVE; DITHIOACETAL; OXATHIOACETAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; RACEMIZATION; SYNTHESIS;

EID: 3843084917     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200025627     Document Type: Article

References (12)

1. Greene, T.W. Protective Groups in Organic Synthesis; John Wiley and Sons: New York, 1981.
2. Dardoize, F.; Gaudemar, M.; Goasdoue, N. A new method of methoxymethylation. Synthesis 1977, 567-568.
3. Hiskey, R.G.; Tucker, W.P. Studies on the synthesis of open-chain unsymmetrical cystine derivatives. Chemistry of aliphatic disulfides. IV. J. Am. Chem. Soc. 1962, 84, 4789-4794.
4. Brownlee, P.J.E.; Cox, M.E.; Handford, B.O.; Marsden, J.C.; Young, G.T. Amino-acids and peptides. Part XX. S-Benzylthiomethyl-L-cysteine and its use in the synthesis of peptides. J. Chem. Soc. 1964, 3832-3840.
5. Corey, E.J.; Seebach, D. Phenylthiomethyllithium and bis(phenylthio)- methyllithium. J. Org. Chem. 1966, 31, 4097-4099.
6. Truce, W.E.; Roberts, F.E. The metalation and alkylation of mercaptals. J. Org. Chem. 1963, 23, 961-964.
7. Corey, E.J.; Seebach, D. Synthesis of pteridine N-oxide. Angew. Chem. Int. Ed. Engl. 1965, 4, 1075-1077.
8. Perriel, H.; Huyer, G.; Young, R.N. Diastereoselective alkylation of carbanions derived from 1,3-oxathianes. Tetrahedron Lett. 1992, 33, 725-728.
9. Fieser, M.; Fieser, L.F. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1972; Vol. 3, 227-228.
10. Buehler, C.A.; Kirchner, F.K.; Deebel, G.F. Org. Synthesis Coll. Vol. 3; 468-469.
11. (a) Amato, J.S.; Karady, S.; Sletzinger, M.; Weinstock, L.M. A new preparation of chloromethyl methyl ether free of bis[chloromethyl]ether. Synthesis 1979, 970-971;
12. (b) Zaidi, J.H. A convenient preparation of n-butyl chloromethyl ether and its use in ortho-directed metallation of phenols. Synth. Comm. 1996, 26, 2407-2419.