1173199-90-0

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 188975-30-6 5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 

Downstream Products

• 1173199-91-1 (1R)-1-[(2R)-5,6-dihydro-2H-pyran-2-yl]-3-phenyl-propan-1-ol 
• 1173199-92-2 3-benzyloxy-(1R)-1-[(2R)-5,6-Dihydro-2H-pyran-2-yl]-propan-1-ol 
• 1173199-93-3 (1R)-[(2R)-5,6-dihydro-2H-pyran-2-yl]-phenyl-methanol 

Relevant academic research and scientific papers

α-Hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine

(Chemical Equation Presented) An efficient catalytic enantioselective preparation of synthetically useful pyranyl and piperidinyl allylic boronates was achieved via a palladium-catalyzed borylation/isomerization reaction on the corresponding alkenyl triflates. The influence of the base and solvent was found to be crucial on the regio- and enantioselectivity of this reaction. The overall borylation process constitutes a successful example of formal asymmetric isomerization of allylic ether/amine. The resulting allylic boronate reagents add to various aldehydes in a one-pot process to give synthetically useful alpha-hydroxyalkyl derivatives in high stereoselectivity.