90288-85-0

Basic information

• Product Name: Cyclopropanecarboxylic acid, 3-methyl-2-phenyl-2-[(trimethylsilyl)oxy]-, methyl ester
• CAS NO: 90288-85-0
• Molecular Formula: C15H22O3Si
• Molecular Weight: 278.423
• Mol File: 90288-85-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarboxylic acid, 3-methyl-2-phenyl-2-[(trimethylsilyl)oxy]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 3-methyl-2-phenyl-2-[(trimethylsilyl)oxy]-, methyl ester(90288-85-0)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 3-methyl-2-phenyl-2-[(trimethylsilyl)oxy]-, methyl ester(90288-85-0)

Safety Data

• Hazardous Substances Data: 90288-85-0(Hazardous Substances Data)

Upstream product

• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 6832-16-2 methyl diazoacetate 

Downstream Products

• 90410-48-3 1,t-3-Dimethyl-c-2-phenyl-t-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 
• 69573-51-9 3-Methyl-4-phenylbutansaeure-methylester 
• 72315-95-8 methyl 3-methyl-4-oxo-4-phenylbutanoate 

Relevant articles and documents

Synthesis of Optically Active Siloxycyclopropanes by Asymmetric Catalysis, I. - Influence of the Catalyst on the Cyclopropanation of (Z)-1-Phenyl-1-(trimethylsiloxy)prop-1-ene

The cyclopropanation of silyl enol ether 1a with methyl diazoacetate (2a) and diazoesters 2b-d in the presence of optically active copper salicylimine complexes 4-Cu was systematically studied.Up to 88percent enantiomeric excess in products 3 were obtained by employing the appropriate reaction conditions and the optimal catalyst ligands.Thus, for the first time respectable optical yields were achieved in asymmetric cyclopropanations of silyl enol ethers with easily available copper-Schiff base catalysts.The ring opening of the separated diastereomers of 3a employing nBu4NF provided methyl γ-oxocarboxylate 6a in good optical purity.This demonstrates that this process occurs without racemization and also that 3a is formed with the same absolute configuration at C-1. - Key Words: Cyclopropanecarboxylates, 2-silyloxy, methyl / Cycloaddition / Enantioselectivity / Asymmetric catalysis / Copper-Schiff base complexes, chiral

Synthesis of 2-Siloxy-substituted Methyl Cyclopropanecarboxylates

2-Siloxy-substituted methyl cyclopropanecarboxylates C - useful building blocks in synthesis - are obtained in great variety and with good yields from the silyl enol ethers E and methyl diazoacetate (D) under copper salt catalysis.Whereas the regiochemical and stereochemical properties of E are completely transferred to the cyclopropanes C, the stereoselectivity concerning the position of the methoxycarbonyl group is low.The 1H and 13C data used to determine the configurations of compounds C are discussed.