82731-65-5

Upstream product

• 136880-73-4 (Z)-but-2-enyldiisopropoxyborane 
• 611-73-4 Benzoylformic acid 
• 82731-57-5 (E)-2-butenyl 2-hydroxy-2-phenylacetate 

Downstream Products

• 82731-75-7 (3RS,4SR,5SR)-3-hydroxy-5-(iodomethyl)-4-methyl-3-phenyl-4,5-dihydro-2(3H)-furanone 
• 82731-76-8 (3RS,4SR,5RS)-3-hydroxy-5-(iodomethyl)-4-methyl-3-phenyl-4,5-dihydro-2(3H)-furanone 
• 82731-75-7 (3RS,4RS,5SR)-3-hydroxy-5-(iodomethyl)-4-methyl-3-phenyl-4,5-dihydro-2(3H)-furanone 

Relevant academic research and scientific papers

The stereoselective crotylboration of alpha-oxocarboxylic acids

Crotylboronates react with alpha-oxocarboxylic acids in a highly stereocontrolled manner. The reaction presumably proceeds through a bicyclic transition state. The alpha-carboxylic substituent exerts a remarkable effect on the rate, regio- and stereoselectivities of the reaction; homoallylic alpha-hydroxycarboxylic acids are formed with regio- and stereoselectivities approach 100%.

Ester-Enolate Claisen Rearrangement of Lactic Acid Derivatives

The ester-enolate Claisen rearrangement of a number of allylic esters of α-hydroxy acids and O-protected derivatives was studied.Crotyl lactate (1b), for example, is converted to the enediolate, silylated, and rearranged to afford the RS,SR and RR,SS dias