Spiro Asymmetric Induction. 3. Synthesis of Optically Pure Syn or Anti α,β-Dihydroxy Esters by the Aldol Condensation of Chiral Glycolate Enolates

Journal of Organic Chemistry

Volumn 52, Issue 14, 1987, Pages 3176-3178

  Pearson, William H ^a   Cheng, Minn Chang ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000578245     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00390a044     Document Type: Article

References (14)

1. For earlier papers, see: (a) Pearson, W. H.; Cheng, M. C.; J. Org. Chem. 1986, 51, 3746–3748. (b) Pearson, W. H.; Cheng, M. C. 1987, 52, 1353.
2. Sharon, N. Complex Carbohydrates: Their Chemistry, Biosynthesis and Function; Addison-Wesley: Reading, MA, 1975. Candy, D. Biological Function of Carbohydrates; Wiley: New York, 1980. Kennedy, J. F.; White, C. A. Bioactive Carbohydrates; Ellis Horwood, Ltd.: Chichester, West Sussex, 1983.
3. Jones, J. K. N.; Szarek, W. A. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; Wiley-Interscience: New York, 1973; Vol. I, Chapter 1. Zamojski, A.; Grynkiewicz, G. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; Wiley-Interscience: New York, 1984; Vol. 6, Chapter 4, pp 141-235. McGarvey, G. J.; Kimura, M.; Oh, T.; Williams, J. M. J. Carbohydr. Chem. 1984, 3, 671.
4. (a) For the only other aldol condensations of a chiral glycolate enolate, see: d'Angelo, J.; Pages, O.; Maddaluno, J.; Dumas, F.; Revial, G.; Tetrahedron Lett. 1983, 25, 5869. (b) For aldol condensations of an achiral glycolate enolate in the presence of a chiral additive, see: Mu-kaiyama, T.; Iwasawa, N. Chem. Lett. 1984, 753. For aldol condensations of achiral glycolate enolates, see: (c) Touzin, A. M. Tetrahedron Lett. 1975, 1477. (d) Takai, K.; Heathcock, C. H. J. Org. Chem. 1985 50, 3247. (e) Gray, B. D.; White, J. D. J. Chem. Soc., Chem. Commun. 1985, 20. (f) Koreeda, M.; Luengo, J. I. J. Org. Chem. 1984, 49, 2079 and references therein.
5. For aldol condensations of higher a-hydroxy acid derivatives (i.e., lactic, mandelic, etc.), see: (a) Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pilli, R.; Badertscher, U.; J. Org. Chem. 1985, 50, 2095–2105, and earlier work cited therein. (b) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Marki, H. P. ; Montgomery, S. H. J. Am. Chem. Soc. 1984,106, 8161–8174, and earlier work cited therein. (c) Heathcock, C. H.; Montgomery, S. H. Tetrahedron Lett. 1985, 26, 1001–1004. (d) Schultz, A. G.; Yee, Y. K. J. Org. Chem. 1976, 41, 4044–4045. (e) Seebach, D.; Coquoz, M. Chimia 1985, 39, 20–22. (f) Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40, 1313-1324, and references to earlier work by Seebach and others cited therein.
6. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060-7067. (b) Roush, W. R.; Michaelides, M. R. Tetrahedron Lett. 1986, 27, 3353-3356. (c) Roush, W. R.; Harris, D. J.; Lesur, B. M. 1983,24, 2227-2230. (d) Wuts, P. G. M.; Bigelow, S. S. J. Org. Chem. 1983, 48, 3489. (e) McGarvey, G. J.; Kimura, M. 1982, 47, 5420-5422. (f) Hoffmann, R. W.; Metternich, R. Liebigs Ann. Chem. 1985, 2246-2460. (g) Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28,139-142. (h) Koreeda, M.; Tanaka, Y. 1987, 28, 143-146.
7. Heathcock5chas examined such an approach to racemic carbohydrates based on the aldol condensation of lactate enolates. For a related approach, see: (a) David, S.; Lepine, M. C. ; Aranda, G.; Vass, G.; J. Chem. Soc., Chem. Commun. 1976, 747. (b) David, S.; Lepine, M. C. J. Chem. Soc., Pprkin Trans. 1 1980, 1262.
8. (a) Evans, D. A.; Nelson, J. V.; Taber, T. R.; Top. Stereochem. 1982, 13, 1. (b) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 111–211. (c) Mukai-yama, T Org. React. (N. Y.) 1982, 28, 203.
9. Evans.,D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975–3978. For a discussion of the transition state, see ref 9a.
10. Yamamoto Y.; Maruyama, K.; Tetrahedron Lett. 1980, 21, 4607–4610.
11. Dale, J. A.; Dull, D. L.; Mosher, H. S.; J. Org. Chem. 1969, 34, 2543.
12. Collet, A. Bull. Soc. Chem. Fr. 1975, 215-219.
13. For racemic syn- and anti-ethyl 2,3-dihydroxyhexanoic acid, see: (a) Mori, N.; Omura, S.; Tsuzuki, Y. Bull. Chem. Soc. Jpn. 1965, 38, 2199–2201. (b) English, J., Jr.; Heywood, D. L. J. Am. Chem. Soc. 1955, 77. 4661–4664.
14. Dalby, S.; Kenner, G. W.; Sheppard, R. C. J. Chem. Soc. 1960, 1, 968-973.