1352127-75-3

Upstream product

• 109-72-8 n-butyllithium 
• 82954-89-0 ethylboronic acid pinacol ester 
• 1352127-71-9 3-phenyl-1-(tributylstannyl)propyl 2,4,6-triisopropylbenzoate 
• 246021-86-3 C₆H₅CH₂CH₂CH(Sn(CH₂CH₂CH₂CH₃)3)OCON(CH(CH₃)2)2 
• 122-97-4 3-Phenyl-1-propanol 
• 1352127-71-9 (S)-3-phenyl-1-(tributylstannyl)propyl 2,4,6-triisopropylbenzoate 
• 218601-55-9 3-phenylpropyl N,N-diisopropylcarbamate 

Downstream Products

• 1992-50-3 1-phenylpentan-3-ol 
• 105836-17-7 (R)-1-phenyl-3-pentanol 
• 71747-37-0 (S)-1-phenylpentan-3-ol 

Relevant academic research and scientific papers

Synthesis of α-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes

Vinyl boron ate complexes of enantioenriched secondary alkyl pinacolboronic esters undergo stereospecific radical-induced 1,2-migration in radical polar crossover reactions. In this three-component process various commercially available alkyl iodides act as radical precursors and light is used for chain initiation. Subsequent oxidation and protodeborylation leads to valuable α-chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.

Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

(-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate. The Royal Society of Chemistry 2011.

Lithiated carbamates: Chiral carbenoids for iterative homologation of boranes and boronic esters

(Chemical Equation Presented) Take your pick: Either enantiomer of either diastereomer of substrates bearing adjacent stereogenic centers is accessible through reaction of an (R)- or (S)-lithiated carbamate with an (R)- or (S)-boronic ester (see scheme; pin = pinacolate, OCb = substituted carbamate).