Acyclic 1,4-stereocontrol via reductive 1,3-transpositions.
One-pot reduction/allylic diazene rearrangement of lactic acid- and mandelic acid-derived alpha,beta-unsaturated tosyl hydrazones leads to 1,4-syn- or 1,4-anti-E-2-alkenyl arrays in high yield and diastereoselectivity. Either the syn or the anti diastereomer can be prepared by choosing the appropriate alkene stereoisomer of the hydrazone. The E-alkenes led to the 1,4-syn isomers, while the Z-alkenes led to the 1,4-anti isomers, both with > or =20:1 diastereoselectivity.
Qi
Wei
W
119 Chemistry Building, University of Arkansas, Fayetteville, Arkansas 72701, USA.
McIntosh
Matthias C
MC
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D007094:Imides; C038867:diazene