A facile and efficient direct aldol addition of simple thioesters

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1503-1506

  Yost, Julianne M ^a   Zhou, Guoqiang ^a   Coltart, Don M ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645951651     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060413q     Document Type: Article

References (12)

1. (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; 2 Vols.
2. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. 3, p 997-1065.
3. (a) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
4. (b) Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127-1130.
5. (c) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
6. (d) Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852-2853.
7. (e) Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284-7285.
8. a of the thioester α-proton has been reported to be 2 units less than that of a corresponding oxoester. See: Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218-4223.
9. All thioesters used in this work, with the exception of commercially available 5, 8, 9. and 29, were prepared via acylation of the corresponding commercially available thiols. See the Supporting Information.
10. Wei, H.-X.; Li, K.; Zhang, Q.; Jasoni, R. L.; Hu. J.; Paré, P. W. Helv. Chim. Acta 2004, 87, 2354-2358.
11. 2 was omitted gave only starting material after 2 days. Likewise, omission of base gave no product.
12. Aldrich. ACS reagent grade, ≥99.5%.