A direct aldol addition of simple thioesters employing soft enolization

Synthesis

Volumn , Issue 3, 2007, Pages 0478-0482

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

^a DUKE UNIVERSITY   (United States)

Author keywords

Direct aldol reaction; Ester; Magnesium; Thioester; Thiol

Indexed keywords

ENOLIZATION; N,N DIISOPROPYLETHYLAMINE; THIOESTERS;

ADDITION REACTIONS; ALDEHYDES; AMINES; DICHLOROMETHANE; ETHERS; MAGNESIUM COMPOUNDS;

ESTERS;

2 METHOXYPHENYL THIOACETATE; ALDEHYDE; BROMIDE; DICHLOROMETHANE; ETHER; ETHYLAMINE; MAGNESIUM; REAGENT; THIOESTER; UNCLASSIFIED DRUG;

AIR TEMPERATURE; ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 33947515409     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958959     Document Type: Article

References (11)

1. (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
2. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999.
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7. (e) Magdziak, D.; Lalic, G.; Lee, H. M.; Former, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284.
8. Yost, J. M.; Zhou, G.; Coltart, D. M. Org. Lett. 2006, 8, 1503.
9. a of the thioester α-proton has been reported to be 2 units less than that of a corresponding ester, see: Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218.
10. All thioesters used in this work, with the exception of commercially available 7, 10, and 11, were prepared via acylation of the corresponding commercially available thiols.
11. Aldrich ACS reagent grade, ≥99.5%.