1613405-33-6

Basic information

• Product Name: (S)-4,4,5,5-tetramethyl-2-(4-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane
• Synonyms: (S)-4,4,5,5-tetramethyl-2-(4-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane
• CAS NO: 1613405-33-6
• Molecular Weight: 288.238
• Mol File: 1613405-33-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-4,4,5,5-tetramethyl-2-(4-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4,4,5,5-tetramethyl-2-(4-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane(1613405-33-6)
• EPA Substance Registry System: (S)-4,4,5,5-tetramethyl-2-(4-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane(1613405-33-6)

Safety Data

• Hazardous Substances Data: 1613405-33-6(Hazardous Substances Data)

Upstream product

• 1338073-31-6 3-phenylpropyl 2,4,6-triisopropylbenzoate 
• 76347-13-2 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 959685-40-6 N,N-diisopropyl-carbamic acid isobutyl ester 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 

Downstream Products

• 1613405-42-7 (S)-2-(4-methyl-1-phenylpentan-3-yl)furan 

Relevant articles and documents

Synthesis of enantioenriched alkylfluorides by the fluorination of boronate complexes

The enantiospecific conversion of chiral secondary boronic esters into alkylfluorides is reported. Boronate complexes derived from boronic esters and PhLi were used as nucleophiles, with Selectfluor II as the electrophilic fluorinating agent, to afford alkylfluorides in short reaction times. The addition of styrene as a radical trap was found to enhance enantiospecificity. A broad range of alkyl boronic esters were converted into alkylfluorides with almost complete enantiospecificity by this method.

Enantiospecific Synthesis of ortho-Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence

Coupling reactions between benzylamines and boronic esters have been investigated. ortho-Lithiated benzylamines react with boronic esters and a N-activator to afford ortho-substituted benzylic boronic esters with formal 1,1′-benzylidene insertion into the C-B bond. The reaction occurs by a SN2′ elimination and 1,2-metalate rearrangement of the N-activated boronate complex to afford a dearomatized intermediate, which undergoes a Lewis-acid catalyzed 1,3-borotropic shift to afford the boronic ester products in high yield and with excellent enantiospecificity. The use of enantioenriched α-substituted benzylamines gave the corresponding secondary boronic esters with high ee.