Diastereoselective Baylis-Hillman reaction: First use of chiral 2,3-epoxy aldehydes as novel electrophiles

Tetrahedron Letters

Volumn 45, Issue 42, 2004, Pages 7847-7850

  Krishna, Palakodety Radha ^a   Lopinti, Krishna Rao ^a   Kannan, V ^a  

^a Discovery Laboratory   (India)

Author keywords

2,3 Epoxy aldehyde; Activated alkene; Chiral electrophile; Cornforth model; Diastereoselective Baylis Hillman reaction

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE;

ARTICLE; BAYLIS HILLMAN REACTION;

EID: 4644275848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.166     Document Type: Article

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20. 1H NMR spectra of the adducts resulting from the trans 2,3-epoxy aldehydes showed the allylic proton (both for syn- and anti-isomers) resonating downfield when compared to the adducts obtained from cis-2,3-epoxy aldehydes
21. 4) and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, 8.5:1.5-8:2, n-hexane-EtOAc) to afford products 1a, 2b, 3a, b, 4a, b, 5a, b, 6a, b, and 7a,b in good yields (61-80%)
22. 3: C, 69.48, H, 6.61; found: C, 69.36, H, 6.59