1452772-73-4

Upstream product

• 23473-12-3 cyclopentyl-lithium 
• 654077-26-6 (2R)-1,2-O-cyclohexylidene-3-phenylpropan-3-one 
• 32916-51-1 cyclopentylmagnesium chloride 
• 78008-36-3 (R)-2,3-cyclohexylideneglyceraldehyde 
• 100-58-3 phenylmagnesium bromide 
• 76779-67-4 1,2,5,6-di-O-cyclohexylidene-D-mannitol 

Downstream Products

• 1452772-66-5 (2S,3S)-1-chloro-3-(2-ethoxyphenoxy)-3-phenylpropan-2-ol 
• 1452772-75-6 (2R,3S)-3-(2-ethoxyphenoxy)-1,2-O-cyclohexylidene-3-phenylpropane 
• 98819-70-6 (+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane 
• 1452772-76-7 (2R,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 98769-72-3 (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide 
• 1356958-71-8 {[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate 
• 1250978-71-2 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate 
• 868686-69-5 (2R,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine 
• 71620-89-8 (S,S)-reboxetine 
• 1452772-74-5 (2R,3R)-1,2-O-cyclohexylidene-3-acetoxy-3-phenylpropane 

Relevant academic research and scientific papers

Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: Applications in the synthesis of reboxetine

A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention of configuration, as against conventional Mitsunobu reaction which generates epoxides with inversion. The methodology was successfully used as a key step in the synthesis of optically active diastereoisomers of the antidepressant drug reboxetine from (R)-2,3-O- cyclohexylidene-d-glyceraldehyde in ～43% overall yields. The Royal Society of Chemistry.

Metal-dependent reaction tuning with cyclopentylmetal reagents: Application to the asymmetric synthesis of (+)-α-conhydrine and (S)-2-cyclopentyl-2- phenylgrycolic acid

The reaction profile of the cyclopentyl organometallic reagents with the aliphatic ketones can be tuned to reduction or addition by changing the metal atom. Cyclopentylmagnesium bromide (CPMB) reduces aromatic and aliphatic aldehydes and ketones to the corresponding alcohols without any C-C bond formation and shows good diastereoselectivity in the reduction of the substituted cyclic and polycyclic ketones as well as chiral α-oxygenated aliphatic ketones. However, in the presence of 10 mol% of ZnClα 2, the cyclopentylmagnesium halides follow a normal Grignard addition to the ketones to give tertiary alcohols with complete diastereoselectivity. The reductive as well as the addition protocols were used for the asymmetric synthesis of two medicinally important compounds, (+)-α-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid.