An efficient synthesis of enantiomerically enriched aryllactic esters (original) (raw)

1994, Tetrahedron Letters

la-i Acconling to Scheme 1, a variety of arylaldchydes we~c condensed with ethyl chloroacetate to give the glycidic ester (0.95 eq. NaN(SiMe3)2, THF, -78' to 0"C). The crude epoxide was submitted without 5205 on a-hydroxy acids 8ce: Brown. H. C.; Pai, G. G.-v, P. K. J. Am. Chem. Sot. 1984.106. 1531. b) plettna. J. J.; Marcotk, P. A.; Kkhwt, H. D.: Stein. H. H.; Grcer, J.; Bolia. G.; Fbmg, A. K. L.: Bopp, 8. A.; Luly. J. R.; Sham, H. L.; Kempf. D. J.; Rosenberg. S. H.; Dellaria, J. F.; De. B.; Merits, I.; Peru, T. J. Med. Chat. 1!388.31,2277. c)stanton. J. L.; Ksander. G. M.; Jesus, R.; Spwbeck, D. M. Biorg. Med. Chem. L&r. 1993,) 539. Manoscriptinpreparation Cohen, S. G.: We.instein,'S. Y. /. Am. Chem. Sot. 1944.86, 5326. L-l-naphthyliactic acid has been prwwed previously from cl-ns~hthylalanik by Hester. J. B.; Pals, D. T.; San& H. H.; !&yer.-T. K.; Schostarez, H.~.;~Thaishvongs. g. Eur. Pat. A&. EP 173,481,1986. Evans, D. A.; h4omiscy. M. hf.; Domw. R. L. J. Am. Ckm. Sw. 1985.107,4346. Akiyami, T.; Nishimoto, H.;&aki, S. Tefrahcdron Len. 1991,32, 1335. Nakamnra. K.; Inow, K.: Ushio, K.: Gka, S.: Ohno. A. J. Org. Chem. 1988.53, 2589. Fim. G. A.; Beight, D. W. Tetmheahn f&r. lN38.29.423. Cony, E. J.; Link, J. 0.; Shao, Y. Tena/&ron La.