- NOUVELLE VOIE D'ACCES STEREOSELECTIVE AUX ESTERS ACRYLIQUES SON APPLICATION EN CHIMIE DES SUCRES
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Regio- and stereo-selective synthesis of an acryl residue by treatment of an allyl alcohol with (Z,E)-1-fluoro-1-methoxy-2-phenylsulfinylpropene was performed in three consecutive reactions in the same flask; displacement of F- by the alcohol, Claisen rearrengement, and dehydrosulfinylation.Thus, 1,5-anhydro-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol gave methyl 3,7-anhydro-6,8-benzylidene-2,4,5-trideoxy-2-C-methylene-D-ribo-oct-4-enonate and methyl 2-O-allyl-4,6-dideoxy-α-D-erythro-hex-4-enopyranoside gave methyl (methyl 2-O-allyl-3,4,6-trideoxy-5-C-methyl-6-C-methylene-α-L-threo-hept-3-enopyranosyd)uronate, which has a chiral quaternary C-5 atom.
- Vatele, Jean-Michel
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p. 177 - 186
(2007/10/02)
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- AN EASY AND EFFICIENT SYNTHESIS OF α-METHYLENE-γ,δ-UNSATURATED ESTERS FROM ALLYLIC ALCOHOLS
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A new method for the regio- and stereo-specific introduction of an acrylic ester unit, via a one pot reaction is described.
- Vatele, Jean-Michel
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p. 1239 - 1242
(2007/10/02)
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- CLAISEN ORTHO ESTER REARRANGEMENT WITH TRIMETHYL β-(METHOXY)ORTOPROPIONATE: A TERMALLY STABLE SYNTHON FOR THE PREPARATION OF METHYL α-SUBSTITUTED ACRYLATES
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Trimethyl β-(methoxy)ortopropionate, a compound which is thermally stable at 190 deg C for proplonged times, may be utilized as a synthon for the preparation of methyl α-substituted acrylates via Claisen ortho ester rearrangement with allylic alcohols followed by β-elimination of methanol with base.
- Raucher, Stanley,Macdonald, James E.,Lawrwence, Ross F.
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p. 4335 - 4338
(2007/10/02)
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