Baylis-Hillman chemistry: synthesis of cis- and trans-α-methylene-γ-lactones

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4187-4189

  Kabalka, George W ^a   Venkataiah, Bollu ^a   Chen, Chunlan ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

Allylboronate; Baylis Hillman; Cross coupling; Homoallylic alcohol; Lactone

Indexed keywords

ALCOHOL DERIVATIVE; LACTONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 33646497000     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.063     Document Type: Article

References (20)

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18. General experimental procedure for trans-α-methylene-lactones: The homoallylic alcohol (1 mmol) was dissolved in dichloromethane (5 mL) and the solution cooled to 0 °C. Carbon tetrabromide (1.5 mmol) and triphenylphosphene (1.5 mmol) were added sequentially, and the reaction mixture allowed to stir at room temperature overnight under a nitrogen atmosphere (reaction monitored by TLC). After completion of the reaction, the solvent was removed and the product was isolated by column chromatography.
19. Yu S.H., Fergusaon M.J., McDonald R., and Hall D.G. J. Am. Chem. Soc. 127 (2005) 12808
20. General experimental procedure for cis-α-methylene-lactones: The homoallylic alcohol (1 mmol) was dissolved in dichloromethane (5 mL) and the solution cooled to 0 °C. p-Toluenesulfonic acid (0.1 mmol) was added, and the reaction mixture allowed to stir at room temperature overnight under a nitrogen atmosphere (reaction monitored by TLC). After completion of the reaction, the solvent was removed and the product was isolated by column chromatography.