A radical approach to asymmetric aldol synthesis

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6754-6755

  Garner, Philip ^a   Leslie, Raymond ^a   Anderson, James T ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001664912     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961499b     Document Type: Article

References (14)

1. Review: Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-338.
2. Cf. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 7585-7591.
3. (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078.
4. (b) Carreira, E. M.; Singer, R. A.; Lee, W. Ibid. 1994, 116, 8837-8838.
5. (c) Keck, G. E.; Krishnamurthy, D. Ibid. 1995, 117, 2363-2364.
6. There is some evidence that a SET mechanism can intervene with aromatic aldehydes: Ashby, E. C.; Argyropoulos, J. N. J. Org. Chem. 1986, 51, 472-476.
7. Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183-4184.
8. Racemic α-hydroxy esters 1b and 1c were conveniently prepared from their cyanohydrins: Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem. Soc., Chem. Commun. 1973, 55-56.
9. Barton, D. H. R.; Togo, H.; Zard, S. Z. Tetrahedron 1985, 41, 5507-5516.
10. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367-4373.
11. 2COMe (from the hydroxide-catalyzed aldol reaction of RCHO and MeCOMe: Dubois, J. E. Ann. Chim. 1951, 6, 406-486) to tri-O-benzyl-D-glucal.
12. Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749.
13. Cf. Fauve, A.; Veschambre, H. J. Org. Chem. 1988, 53, 5215-5219.
14. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.