104636-85-3

Upstream product

• 72047-94-0 [2-(acetoxymethyl)prop-2-enyl]trimethylsilane 
• 77399-49-6 methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate 

Downstream Products

• 146984-61-4 3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose 

Relevant academic research and scientific papers

New routes to isomerically pure cyclopentanes. Synthesis of (3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-ol using palladium-catalyzed [2 + 3] cycloaddition

Two different routes to the enantiomerically pure (3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-ol (6), a useful intermediate for the synthesis of a number of natural products, are described. Formation of the chiral five-membered ring was achieved using a palladium-catalyzed [2 + 3] cycloaddition between 2-(acetoxymethyl)-3-(trimethylsilyl)propene and optically active methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5- enofuranuronate or ethyl (4R,Z)-4,5-(isopropylidenedioxy)pent-2-enoate.

Diastereoselectivity of a Annulation. On the Question of a Dipole Effect on Diastereoselectivity of Olefin Addition

The stereochemistry of addition to γ-alkoxy-α,β-unsaturated carbonyl systems is examined in the context of a palladium catalyzed cycloaddition.