Diastereoselective Darzens condensations

Tetrahedron Letters

Volumn 48, Issue 17, 2007, Pages 2961-2964

  Achard, Thierry J R ^a   Belokon', Yuri N ^b   Hunt, Jamie ^a   North, Michael ^a   Pizzato, Francesca ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ALDEHYDE; BASE; EPOXIDE; HALIDE; HYDROXIDE; METAL; SOLVENT;

ARTICLE; CIS ISOMER; DARZENS REACTION; DIASTEREOISOMER; SYNTHESIS; TRANS ISOMER;

EID: 33947604610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.010     Document Type: Article

References (9)

1. For a review of the Darzens reaction see:. Rosen T. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 409-439
2. Arai S., Suzuki Y., Tokmaru K., and Shioiri T. Tetrahedron Lett. 43 (2002) 833-836
3. Substrates 1a and 1b were prepared by literature procedures:. Benkli K., Demirayak S., Gundogdu-Karaburun N., Kiraz N., and Iscan G. Indian J. Chem., Sect. B (2004) 174-179
4. Aquino C.J., Armour D.R., Berman J.M., Birkemo L.S., Carr R.A.E., Croom D.K., Dezube M., Dougherty Jr. R.W., Ervin G.N., Grizzle M.K., Head J.E., Hirst G.C., James M.K., Johnson M.F., Miller L.J., Queen K.L., Rimele T.J., Smith D.N., and Sugg E.E. J. Med. Chem. 39 (1996) 562-569
5. +) requires 338.0036.
6. Arai S., Tokumaru K., and Aoyama T. Tetrahedron Lett. 45 (2004) 1845-1848
7. Aggarwal V.K., Charmant J.P.H., Fuentes D., Harvey J.N., Hynd G., Ohara D., Picoul W., Robiette R., Smith C., Vasse J.-L., and Winn C.L. J. Am. Chem. Soc. 128 (2006) 2105-2114
8. THF has previouly been reported to be the solvent of choice to obtain cis-epoxides from Darzens condensations:. Wang Z., Xu L., Mu Z., Xia C., and Wang H. J. Mol. Catal. A 218 (2004) 157-160
9. For a previous report on the use of acetonitrile to obtain trans-selectivity in Darzens condensations using ethyl α-chloroacetamide see:. Wang Z.-T., Xu L.-W., Xia C.-G., and Wang H.Q. Helv. Chim. Acta 87 (2004) 1958-1962