Application of a new tandem isomerization-aldolization reaction of allylic alcohols to the synthesis of three diastereoisomers of (2R)-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetraol.
The tandem isomerization-aldolization reaction of (2R)-1,2-O-isopropylidene-4-penten-1,2,3-triol 3 and formaldehyde gives a mixture of two aldol products 2a and 2b. The stereoselective reduction of each compound by l-Selectride affords two diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol while a third diastereoisomer is obtained by stereoselective reduction with Me(4)NHB(OAc)(3).
Cuperly
David
D
ENSCR, Laboratoire de Synthèses et Activations de Biomolécules, UMR CNRS 6052, 35700 Rennes, France.
Crévisy
Christophe
C
Grée
René
R
D000438:Alcohols / Q000138:chemical synthesis; D000498:Allyl Compounds / Q000138:chemical synthesis; D004149:Dioxoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007536:Isomerism; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism
C481904:1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetraol; D000438:Alcohols; D000498:Allyl Compounds; D004149:Dioxoles; D007202:Indicators and Reagents; D007659:Ketones