Efficient synthesis of quaternary α-hydroxy acids by alkylation of α-ketoamide-derived dienediolates

Synthesis

Volumn , Issue 19, 2005, Pages 3263-3270

  Newton, Rebecca ^a   Marsden, Stephen P ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Alkylations; Dianions; Hydroxy acids; Ketoamides; Stereoselective olefin synthesis

Indexed keywords

ALKYLATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DIANIONS; HYDROXY ACIDS; KETOAMIDES; STEREOSELECTIVE OLEFIN SYNTHESIS;

ORGANIC COMPOUNDS;

2 ALLYL 2 HYDROXY 1 PIPERIDIN 1 YLPENT 3 EN 1 ONE; 2 HYDROXY 1 PIPERIDIN 1 YL 2 (STYRYL)PENT 4 EN 1 ONE; 2 HYDROXY 1 PIPERIDIN 1 YL 2 (STYRYL)PENTAN 1 ONE; 2 HYDROXY 1 PIPERIDIN 1 YL2 PROPYLPENT 3 EN 1 ONE; 2 HYDROXY 2 METHYL 1 PIPERIDIN 1 YLPENT 3 EN 1 ONE; 2 HYDROXY 2 METHYL 4 PHENYL 1 PIPERIDIN 1 YLBUT 3 EN 1 ONE; 2 HYDROXYACID; ACID; ALKADIENE; ALKENE; ALKENE DERIVATIVE; AMIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ISOMER; PROTON TRANSPORT; SYNTHESIS;

EID: 29044432963     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918481     Document Type: Article

References (16)

1. Einsle, O.; Tezcan, F. A.; Andrade, S. L. A.; Schmid, B.; Yoshida, M.; Howard, J. B.; Rees, D. C. Science 2002, 297, 1696.
2. Kusano, A.; Seyama, Y.; Nagai, M.; Shibano, M.; Kusano, G. Biol. Pharm. Bull. 2001, 24, 1198.
3. Dawson, M. J.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; O'Neill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V. J. Antibiot. 1992, 45, 639.
4. Tucker, H.; Crook, J. W.; Chesterson, G. J. J. Med. Chem. 1988, 31, 954.
5. Wing, K. D.; Sacher, M.; Kagaya, Y.; Tsurubuchi, Y.; Mulderig, L.; Connair, M.; Schnee, M. Crop Protection 2000, 19, 537.
6. (a) Naef, R.; Seebach, D. Angew. Chem, 1981, 93, 1113.
7. (b) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704.
8. (c) Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194.
9. (a) Boons, G.-J.; Downham, R.; Kim, K.-S.; Ley, S. V.; Woods, M. Tetrahedron 1994, 50, 7157.
10. (b) Diez, E.; Dixon, D. J.; Ley, S. V. Angew. Chem. Int. Ed. 2001, 40, 2906.
11. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111.
12. Koft, E. R.; Williams, M. D. Tetrahedron Lett. 1986, 27, 2227.
13. Lithium halides are known to influence reactivity of lithium amide bases by deaggregation: (a) De Pue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5518.
14. (b) De Pue, J. S.; Collum, D. B. J. Am. Chem. Soc. 1988, 110, 5524.
15. For previous examples of this approach to α-ketoamides, see: (a) Sibi, M. P.; Sharma, R.; Paulson, K. L. Tetrahedron Lett. 1992, 33, 1941.
16. (b) Burton, A. J.; Caldwell, K. S.; Fuchter, M. J.; Lindvall, M. K.; Patel, R.; Packham, T. W.; Prodger, J. C.; Schilling, M. B.; Walker, M. D. Tetrahedron Lett. 2003, 44, 5653.