Overcoming intrinsic diastereoselection using polyleucine as a chiral epoxidation catalyst

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1779-1782

  Ray, Peter C ^a   Roberts, Stanley M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; EPOXIDE; KETONE DERIVATIVE; LEUCINE; POLYAMINOACID;

ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033605171     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02689-6     Document Type: Article

References (15)

1. 1. Sharpless, K.B. Chem. Scr. 1985, 25, 71.
2. Masamune, S.; Choy, W.; Petersen, J.S. and Sita, L.S. Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
3. 2. Martin, V.S.; Woodard, S.S.; Katsuki, T.; Yamada, Y.; Ikeda, M. and Sharpless, K.B. J. Am. Chem. Soc. 1981, 103, 6237.
4. Katsuki, T.; Lee, A.W.M.; Ma, P.; Martin, V.S.; Masamune, S.; Sharpless, K.B.; Tuddenham, D. and Walker, F.J. J. Org. Chem. 1982, 47, 1373.
5. Minami, N.; Ko, S.S. and Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109.
6. 3. a) Lasterra-Sánchez, M.E.; Roberts, S.M. Current Organic Chemistry, 1997, 1, 187, and references therein (for the biphasic conditions),
7. b) Allen, J.V.; Drauz, K.; Ray, P.C.; Roberts, S.M. and Skidmore, J. unpublished results (for the percarbonate conditions).
8. 4. Jurczak, J.; Pikul, S. and Bauer, T. Tetrahedron 1986, 42, 447.
9. Schmid, C.R. and Bryant, J.D. Org. Synth. 1993, 72, 216.
10. Zhong, Y-L and Shing, T.K.M. J. Org. Chem. 1997, 62, 2622.
11. t = 22 min. Starting from rac-1, the retention times for the products of ent-1 epoxidation are, ent-3: 13 min.; ent-2: 35 min. Validation of the diastereomer ratios was obtained from UV-analysis of the enantiopure epoxides 2 and 3, which afforded replicate chromatograms throughout the HPLC absorption range.
12. 6. The crystal structure of 3 was provided by the E.P.S.R.C. X-Ray Crystallography Service, Department of Chemistry, University of Wales, Cardiff and the details will be reported in a full paper.
13. 7. Krief, A.; Provins, A. and Froidbise, A. Tetrahedron Lett. 1998, 39, 1437.
14. 8. Mulzer, J.; Kappert, M.; Huttner, G. and Jibril, I. Angew. Chem. Int. Ed. Engl. 1984, 23, 704.
15. 3).