133038-72-9

Basic information

• Product Name: (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate
• Synonyms: (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate
• CAS NO: 133038-72-9
• Molecular Weight: 249.353
• Mol File: 133038-72-9.mol

Chemical Properties

• CAS DataBase Reference: (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate(133038-72-9)
• EPA Substance Registry System: (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate(133038-72-9)

Safety Data

• Hazardous Substances Data: 133038-72-9(Hazardous Substances Data)

Upstream product

• 19009-39-3 N,N-diisopropylcarbamoyl chloride 
• 1517-69-7 (R)-1-phenylethanol 
• 133038-74-1 (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate 
• 359868-65-8 1-phenylvinyl N',N'-diisopropylcarbamate 
• 98-86-2 acetophenone 
• 145167-88-0 N,N-diisopropyl carbamic acid (1-phenylethyl) ester 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 133038-76-3 (-)-(R)-methyl-2-(N,N'diisopropylcarbamoyloxy)-2-phenylpropanoate 
• 133038-74-1 (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate 
• 1301717-37-2 C₁₇H₂₅BO₂ 
• 1257661-33-8 4,4,5,5-tetramethyl-2-(2-phenylpent-4-en-2-yl)-1,3,2-dioxaborolane 
• 1240815-92-2 (R)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane 

Relevant articles and documents

Silaboration of [1.1.1]Propellane: A Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives

The silaboration of [1.1.1]propellane enables direct introduction of B and Si functional groups onto the bicyclo[1.1.1]pentane (BCP) scaffold in high yield under mild, additive-free conditions. The silaborated BCP can be obtained on a gram-scale in a single step without the need for column-chromatographic purification, and is storable and easy to handle, providing a versatile synthetic intermediate for BCP derivatives. We also describe various conversions of the C?B/C?Si bonds on the BCP scaffold, including development of a modified Suzuki–Miyaura cross-coupling reaction at the highly sterically hindered bridgehead sp3 carbon center of the BCP skeleton using a combination of highly activated BCP boronic esters, copper(I) oxide, and a PdCl2(dppf) catalyst system.

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.

Enantioselective Rh-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites

(Chemical Equation Presented) Monodentate phosphoramidites, in particular PipPhos and its octahydro analogue, are excellent ligands for the rhodium-catalyzed asymmetric hydrogenation of aromatic enol acetates, enol carbamates, and 2-dienol carbamates up to 98% ee. These latter substrates were hydrogenated selectively to the carbamates of the allyl alcohol.

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