Non-thiazolidinedione antihyperglycemic agents. Part 5: asymmetric aldol synthesis of (S)-(-)-2-oxy-3-arylpropanoic acids.

David Haigh, H.C. Birrell, B.C.C. Cantello, D.S. Eggleston, R.C. Haltiwanger, R.M. Hindley, A. Ramaswamy, N.C. Stevens

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Abstract

Haigh, David; Birrell, Helen C.; Cantello, Barrie C. C.; Eggleston, Drake S.; Haltiwanger, R. Curtis; Hindley, Richard M.; Ramaswamy, Anantha; Stevens, Nicola C. Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, Essex, UK. Tetrahedron: Asymmetry (1999), 10(7), 1353-1367. Publisher: Elsevier Science Ltd., CODEN: TASYE3 ISSN: 0957-4166. Journal written in English. CAN 131:144537 AN 1999:369514 CAPLUS (Copyright (C) 2009 ACS on SciFinder (R)) Abstract Boron-mediated asym. aldol reactions of 4-[2-(2-benzoxazolylmethylamino)ethoxy]benzaldehyde with 2-oxyethanoyloxazolidinones contg. electron withdrawing, chelating, and bulky alkoxy and aryloxy groups, gave variable yields of syn-aldol adducts in high diastereoisomeric excess. These adducts were dehydroxylated in a sequence which complements the traditional Evans asym. alkylation strategy. Cleavage of the auxiliary from these intermediates afforded antihyperglycemic (S)-(-)-2-oxy-3-arylpropanoic acids in excellent enantiomeric excess. The target compds. were ?-alkoxy-4-[2-[(benzoxazolyl)amino]ethoxy]benzenepropanoic acid derivs. The biol. activity of the compds. thus prepd. was not reported here.
Original languageEnglish
Pages (from-to)1353-1367
Number of pages15
JournalTetrahedron-Asymmetry
Volume10
Publication statusPublished - 1999

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    Haigh, D., Birrell, H. C., Cantello, B. C. C., Eggleston, D. S., Haltiwanger, R. C., Hindley, R. M., Ramaswamy, A., & Stevens, N. C. (1999). Non-thiazolidinedione antihyperglycemic agents. Part 5: asymmetric aldol synthesis of (S)-(-)-2-oxy-3-arylpropanoic acids. Tetrahedron-Asymmetry, 10, 1353-1367.