78019-47-3

Upstream product

• 4286-15-1 (S)-2-phenylbutyric acid 
• 33442-47-6 (S)-2-phenylbutan-1-ol 
• 38554-58-4 (S)-(+)-1-chloro-2-phenylbutane 
• 1201898-79-4 (S)-2-(3-phenylhex-5-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-70-5 (S)-N,N-diisopropylcarbamic acid 1-phenylpropyl ester 

Relevant academic research and scientific papers

Protodeboronation of tertiary boronic esters: Asymmetric synthesis of tertiary alkyl stereogenic centers

While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF?3H2O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. The methodology has been applied to a short synthesis of the sesquiterpene, (S)-turmerone.

Remote stereocontrol by sulfinyl groups: Asymmetric alkylation of chiral 2-p-tolylsulfinyl benzyl carbanions

Alkylation reactions of the benzyllithiums derived from enantiomerically pure 2-p-tolylsulfinyl alkylbenzenes have been carried out with excellent yields and high de. A lithiation-substitution sequence, stereochemically controlled by a remote sulfoxide, accounts for the experimental results.