Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of alpha,beta-unsaturated esters from aldehydes.
The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH(2)Cl(2), rt or -78 degrees C) to yield alpha,beta-unsaturated esters; aryl aldehydes and aliphatic aldehydes possessing significant chain branching elements gave trans alkene products with high stereoselectivity (E : Z up to >98 : 2), while straight chain aliphatic aldehydes gave cis products preferentially (Z : E up to 92 : 8).
Blakemore
Paul R
PR
School of Chemistry, University of Leeds, West Yorkshire, UK. paul.blakemore@science.oregonstate.edu
Ho
Danny K H
DK
Nap
W Mieke
WM
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D052160:Benzothiazoles / Q000737:chemistry*; D002087:Butyrates / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
C508635:6-(nitrooxy)hexyl-(2z)-4-(acetyloxy)-3-(4-(methylsulfonyl)phenyl)-2-phenylbut-2-enoate; D000085:Acetates; D000447:Aldehydes; D000475:Alkenes; D052160:Benzothiazoles; D002087:Butyrates; D004952:Esters; D009574:Nitro Compounds; D013450:Sulfones; C511163:ethyl (benzothiazol-2-ylsulfonyl)acetate