821784-98-9

Basic information

• Product Name: Carbamic acid, bis(1-methylethyl)-, (1S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl ester
• CAS NO: 821784-98-9
• Molecular Formula: C22H36BNO4
• Molecular Weight: 389.343
• Mol File: 821784-98-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, bis(1-methylethyl)-, (1S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, bis(1-methylethyl)-, (1S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl ester(821784-98-9)
• EPA Substance Registry System: Carbamic acid, bis(1-methylethyl)-, (1S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl ester(821784-98-9)

Safety Data

• Hazardous Substances Data: 821784-98-9(Hazardous Substances Data)

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 218601-55-9 3-phenylpropyl N,N-diisopropylcarbamate 
• 19009-39-3 N,N-diisopropylcarbamoyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 14097-24-6 (R)-1,3-diphenylpropanol 
• 14097-24-6 (S)-1,3-diphenylpropanol 
• 24536-68-3 (E)-2,3,2',3'-tetrahydro-[1,1']biindenylidene 
• 77063-35-5 (E)-2,5-diphenylprop-2-ene 

Relevant articles and documents

Stereospecific Synthesis of Alkenes by Eliminative Cross-Coupling of Enantioenriched sp3-Hybridized Carbenoids

1-Aryl-1,2-dialkylethenes were generated by a sequence of electrophilic substitution, 1,2-metalate rearrangement, and β-elimination initiated by the addition of enantioenriched α-(carbamoyloxy)alkylboronates to enantioenriched lithiated carbamates. The carbenoid stereochemical pairing [i.e., “like”=(S)+(S) or “unlike”=(S)+(R)] and the elimination mechanism (syn or anti), not substituent effects, determined the configuration of the trisubstituted alkene target. For example, (Z)-2,5-diphenyl-2-pentene was produced in 70 % yield with E/Z=5:95 by a like combination of Li and B carbenoids and syn (thermal) elimination whereas the E isomer was obtained in the same yield with E/Z>98:2 by an otherwise identical process involving an unlike stereochemical pairing. The concept elaborated overcomes an intrinsic limitation of traditional strategies for direct connective alkene synthesis, which cannot realize meaningful stereochemical bias unless the alkene substituents are strongly differentiated.

Stereospecific reaction of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with grignard reagents - Synthesis of highly enantioenriched secondary alcohols

Highly enantioenriched secondary alcohols were synthesized by treatment of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with Grignard reagents. An intermediary boronate complex was transformed stereospecifically to the corresponding secondary 2-alkenyl- and alkylboronates by migration of an introduced residue. Oxidative workup furnished the enantioenriched secondary alcohols.