439937-71-0

Upstream product

• 929568-27-4 3-hydroxy-hex-5-enoic acid methoxy-methyl-amide 
• 75-16-1 methylmagnesium bromide 
• 100636-39-3 methyl 3-carbonyl-5-hexenoate 
• 439937-69-6 4-(hydroxydimethylsilyl)-6-hepten-2-one 
• 162613-57-2 methyl 3-hydroxyhex-5-enoate 
• 99183-20-7 (+/-)-2-methyl-2-(2-hydroxy-4-penten)-1,3-dioxolane 
• 439937-70-9 1,1'-bis(2-oxo-6-hepten-4-yl)tetramethyldisiloxane 

Downstream Products

• 19781-76-1 (2RS,4SR)-6-heptene-2,4-diol 
• 19781-76-1 (2RS,4RS)-6-heptene-2,4-diol 

Relevant academic research and scientific papers

Diastereoselective Hydroxyethylation of β-Hydroxyketones: A Reformatsky Cyclization-Lactone Reduction Cascade Mediated by SmI2?H2O

The hydroxyethylation of β-hydroxyketones allows diastereoselective access to important 1,3,5-triols. The approach exploits a SmI2?H2O-mediated Reformatsky cyclization-lactone reduction cascade.

An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones

A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehyd

Enantioselective microbial hydrolysis of dissymmetrical cyclic carbonates with disubstitution

Enantioselective microbial hydrolysis of C1 and C2 dissymmetrical cyclic carbonates with disubstitution (methyl and another groups) has been developed. Pseudomonas diminuta (FU0090), a bacterium, efficiently catalyzes the hydrolysis of five-membered cyclic carbonates. While the trans-substrates are hydrolyzed with low enantioselectivities and/or reactivities, the microbe hydrolyzes the cis-substrates with very high enantioselectivities to afford the corresponding almost optically pure anti-(2R,3S)-diols. On the other hand, six-membered trans-cyclic carbonates are enantioselectively hydrolyzed to afford the corresponding optically active syn-(2R,4R)-diols, although the hydrolysis of the cis-substrates gives racemic compounds. In all cases, the enzyme prefers the (R)-enantiomer for the carbon atom bearing a methyl group.

Novel rearrangements of 4-silyl-3-buten-2-ones

Two-4-silyl-3-buten-2-ones, 2a, and 2c, underwent an interesting rearrangement involving migration of the allyl or phenyl group on the silicon atom to the adjacent enone carbon when treated with various bases.