A rapid, simple route to homochiral α,β-epoxyketones

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 6069-6072

  Meth Cohn, Otto ^a   Chen, Yi ^a  

^a UNIVERSITY OF SUNDERLAND   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE DERIVATIVE; ORGANOLITHIUM COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; DIASTEREOISOMER; EPOXIDATION; STEREOCHEMISTRY;

EID: 0033551681     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01260-5     Document Type: Article

References (14)

1. Meth-Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc. Perkin 1 1988, 2663-2674.
2. e.g. see Julia, S.; Masana, J.; Vega, J. C. Angew. Chem, Int. Ed. Engl. 1980, 19, 929;
3. Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090-8091;
4. Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602;
5. Chen, W. P.; Roberts, S. M., J. Chem. Soc. Perkin Trans. 1 1999, 103-105;
6. Elston, C. L.,; Jackson, R. F. W.; Macdonald, S. F. J.; Murray, P. J. Angew. Chem, Int. Ed. Engl. 1997, 36, 410-412 and references therein.
7. Short, R. P.; Kennedy, R. M.; Masamune, S. J. Org. Chem. 1989, 54, 1755-1756.
8. From Fluka
9. Chiralcel OD columns were used at 254nm with hexane/IPA(95/5) as mobile phase at a flow rate of 1.0 mL/min. The racemic substrate was compared with the homochiral material. A Gilson HPLC system was employed.
10. 3 was utilised.
11. Colonna, S.; Molinari, H.; Banfi, S. Tetrahedron 1983, 39, 1635-1641.
12. 4, evaporated, and the residue purified by flash chromatography (light petroleum/ diethyl ether 3:1).
13. Hill, J. G.; Rossiter, B. E; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607-3608.
14. Itsuno, S.; Sakakura, M.; Ito, K. J. Org. Chem. 1990, 55, 6047-6049.