67679-06-5

Basic information

• Product Name: Benzeneacetaldehyde, a-methyl-a-2-propenyl-, (R)-
• CAS NO: 67679-06-5
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol File: 67679-06-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: Benzeneacetaldehyde, a-methyl-a-2-propenyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetaldehyde, a-methyl-a-2-propenyl-, (R)-(67679-06-5)
• EPA Substance Registry System: Benzeneacetaldehyde, a-methyl-a-2-propenyl-, (R)-(67679-06-5)

Safety Data

• Hazardous Substances Data: 67679-06-5(Hazardous Substances Data)

Upstream product

• 15727-80-7 allyl 4-nitrobenzoate 
• 130203-11-1 (S)-2-[(Diphenylphosphanyl)-methyl]-1-((Z)-2-phenyl-propenyl)-pyrrolidine 
• 130203-10-0 allyl o-toluenesulfonate 
• 107-05-1 3-chloroprop-1-ene 
• 24401-39-6 2-methyl-2-phenyl-pentenal 
• 34713-70-7 2-Phenylpropanal 
• 33215-90-6 isopropyl-(2-phenyl-propylidene)-amine 
• 60261-46-3 (2S)-2-[(diphenylphosphino)methyl]pyrrolidine 
• 591-87-7 Allyl acetate 
• 6728-21-8 allyl mesylate 
• 88224-01-5 L-valine allyl ester 
• 15784-26-6 allyl t-butyl carbonate 
• 1342313-03-4 (R)-2-methyl-2-phenyl-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanal 
• 107-18-6 allyl alcohol 

Relevant articles and documents

Nickel/Enamine Cooperative Catalysis Enables Highly Enantioselective Allylic Alkylation of α-Branched Aldehydes

All-carbon quaternary stereocenters constitute a significant portion of natural products and bioactive compounds. Here we disclose a nickel and chiral amine cooperative catalysis to enable a highly enantioselective allylic alkylation reaction between α-branched aldehydes and a wide scope of allyl esters, allowing the all-carbon quaternary stereocenter to be accessed with excellent enantioselectivity (up to 98% ee) and structural diversity. The general synthetic applicability has been showcased by the enantioselective synthesis of key chiral building blocks to access (+)-eptazocine, (?)-aphanorphine, and other two bioactive compounds.

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Enantioselective α-allylation and -propargylation of α-branched aldehydes with alkyl halides was successfully performed using a chiral primary amino acid organocatalyst. This alkylation reaction, involving the generation of a chiral quaternary carbon stereocenter, proceeded smoothly in a mildly basic aqueous solution of potassium hydrogen carbonate to furnish α-allylated or -propargylated aldehydes in a good yield (up to 87%) and high enantioselectivity (up to 96% ee).

Asymmetric α-allylation of α-branched aldehydes with allyl alcohols by synergistic catalysis using an achiral palladium complex and a chiral primary amino acid

Highly enantioselective direct α-allylation of α-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary α-amino acid. Various α-allylated aldehydes possessing a stereocontrolled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity. Georg Thieme Verlag Stuttgart New York.