Stereoselective synthesis of 2-aryloxy acids from lactamide derived esters of racemic α-halo carboxylic acids

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2683-2686

  Devine, Paul N ^a   Dolling, Ulf H ^a   Heid Jr , Richard M ^a   Tschaen, David M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOXYACETIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029928212     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00391-7     Document Type: Article

References (14)

1. (a) Koh, K.; Durst, T. J. Org. Chem. 1994, 59, 4683.
2. (b) Koh, K.; Ben, R.N.; Durst, T. Tetrahedron Lett. 1993, 34, 4473.
3. For other diastereoselective reactions utilizing pantolactone or ethyl lactate see: (a) Larsen, R.D.; Corley, E.G.; Davis, P.; Reider, P.J.; Grabowski, E.J.J. J. Am. Chem. Soc. 1989, 111, 7650.
4. (b) Koh, K.; Ben, R.N.; Durst, T. Tetrahedron Lett. 1994, 35, 375.
5. (a) Nahm, S.; Weinreb, S.M. Tetrahedron Lett. 1981, 22, 3815.
6. (b) Basha, A.; Lipton, M.; Weinreb, S.M. Tetrahedron Lett. 1977, 28, 4171.
7. Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
8. (a) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799.
9. (b) Harpp, D.N.; Bao, L.Q.; Black, C.J.; Gleason, J.G.; Smith, R.A.; J. Org. Chem. 1975, 40, 3420.
10. All new compounds described in this article displayed satisfactory analytical data.
11. The α-iodoester was prepared by treating the α-bromoester with NaI in acetone.
12. Corey, E.J.; Link, J.O. Tetrahedron Lett. 1992, 33, 3431.
13. For other asymmetric syntheses of α-hydroxy acids and esters see: (a) Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983; Chapter 2.
14. (b) Singh, V.K. Synthesis 1992, 605.