133038-74-1

Basic information

• Product Name: (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate
• Synonyms: (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate
• CAS NO: 133038-74-1
• Molecular Weight: 249.353
• Mol File: 133038-74-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate(133038-74-1)
• EPA Substance Registry System: (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate(133038-74-1)

Safety Data

• Hazardous Substances Data: 133038-74-1(Hazardous Substances Data)

Upstream product

• 133038-72-9 (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 61632-72-2 (4-bromobutyl)boronic acid 
• 98-85-1 1-Phenylethanol 
• 98-86-2 acetophenone 

Downstream Products

• 156943-65-6 (S)-(-)-2-(N,N-diisopropylcarbamoyloxy)-2-phenylpropanol 
• 133038-76-3 (-)-(R)-methyl-2-(N,N'diisopropylcarbamoyloxy)-2-phenylpropanoate 
• 156943-67-8 (-)-(S)-3-(N,N-diisopropylcarbamoyloxy)-3-phenyl-2-butanone 
• 133038-72-9 (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate 
• 156943-61-2 (+)-(R)-S-methyl (R)-2-(N,N-diisopropylcarbamoyloxy)-2-methylpropanedithioate 
• 1201898-74-9 (S)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane 
• 1201898-89-6 (R)-2-[1-(4-chlorophenyl)-1-phenylethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-77-2 (S)-2-(2-phenylpent-4-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-76-1 (S)-2-(2-phenylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-75-0 (S)-2-(2-methyl-3-phenylbut-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-91-0 (R)-2-[1-(4-methoxyphenyl)-1-phenylethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1201898-81-8 (S)-2-(1,2-diphenylpropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

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.

Stereocontrolled synthesis of adjacent acyclic quaternary-tertiary motifs: Application to a concise total synthesis of (-)-filiformin

Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary-tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel-type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps have been applied to the shortest enantioselective synthesis of (-)-filiformin to date (9 steps) with full stereocontrol. True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary-tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel-type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (-)-filiformin.

Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology

The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.

Synthesis of highly enantioenriched C-TERTIARY amines from boronic esters: Application to the synthesis of igmesine

Better than all the rest: Tertiary boronic esters, readily available using the lithiation-borylation reaction, have been converted into tertiary alkylamines in very high ee. The work has been applied to a short, modular, and fully stereocontrolled synthesis of the pharmaceutical igmesine and chiral 2,2-disubstituted piperidines.

Generation of a configurationally stable, enantioenriched α-oxy-α-methylbenzyllithium: Stereodivergence of its electrophilic substitution

The deprotonation of (R)- or (S)-1-phenylethyl N,N-diisopropylcarbamate with s-butyllithium/TMEDA in unpolar solvents (e.g. ether or hexane) at -78°C produces configurationally stable ion pairs which are substituted stereospecifically by different electro