1314581-30-0

Basic information

• Product Name: tert-butyl (1-(4-chlorophenyl)allyl) carbonate
• Synonyms: tert-butyl (1-(4-chlorophenyl)allyl) carbonate
• CAS NO: 1314581-30-0
• Molecular Weight: 268.74
• Mol File: 1314581-30-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: tert-butyl (1-(4-chlorophenyl)allyl) carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1-(4-chlorophenyl)allyl) carbonate(1314581-30-0)
• EPA Substance Registry System: tert-butyl (1-(4-chlorophenyl)allyl) carbonate(1314581-30-0)

Safety Data

• Hazardous Substances Data: 1314581-30-0(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 1289638-90-9 (E)-1-[3-(4-chlorophenyl)allyl]-2,3,4,5,6-pentafluorobenzene 
• 1155875-49-2 (R)-2-(4-chlorophenyl)but-3-en-1-ol 

Relevant articles and documents

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

Formaldehyde N, N-dialkylhydrazones as neutral formyl anion equivalents in iridium-catalyzed asymmetric allylic substitution

The use of formaldehyde N,N-dialkylhydrazones as neutral C1-nucleophiles in the iridium-catalyzed substitution of allylic carbonates is described for two processes. Kinetic resolution or, alternatively, stereospecific substitution affords configurationally stable α,α-disubstituted aldehyde hydrazones in high enantiomeric excess and yield. This umpolung approach allows for the construction of optically active allylic nitriles and dithiolanes as well as branched α-aryl aldehydes. A catalyst-controlled reaction with Enders' chiral hydrazone derivatives followed by diastereoselective nucleophilic addition to the hydrazone products constitutes a two-step stereodivergent synthesis of chiral amines.