127181-22-0

Basic information

• Product Name: (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate
• CAS NO: 127181-22-0
• Molecular Weight: 156.138
• Mol File: 127181-22-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate(127181-22-0)
• EPA Substance Registry System: (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate(127181-22-0)

Safety Data

• Hazardous Substances Data: 127181-22-0(Hazardous Substances Data)

Upstream product

• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 108-59-8 malonic acid dimethyl ester 
• 115314-14-2 (R)-glycidyl nosylate 
• 1440528-08-4 C₁₉H₁₈O₄S 
• 1333379-12-6 C₇H₉ClO₄ 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67843-74-7 (S)-epichlorohydrin 

Downstream Products

• 916069-80-2 (S)-4-fluoromethyldihydro-3H-furan-2-one 
• 127181-31-1 (1R,2S)-1-amino-2-(hydroxymethyl)cyclopropanecarboxylic acid 

Relevant articles and documents

Diastereoselective Iodocarbocyclization Reaction of 8-Phenylmenthyl Allylmalonate: An Efficient Preparation of a Synthetic Intermediate of Cyclopropane Amino Acids

The iodocarbocyclization of allylmalonate using (-)-8-phenylmenthol as a chiral auxiliary proceeded with high diasterreoselectivity to give the iodomethylcyclopropane dicarboxylic ester in good yield.

Dimeric TADDOL Phosphoramidites in Asymmetric Catalysis: Domino Deracemization and Cyclopropanation of Sulfonium Ylides

A gold-catalyzed asymmetric cyclopropanation of unactivated olefins with sulfonium ylides in the presence of a bimetallic catalyst with a novel dimeric TADDOL-phosphoramidite ligand is reported. This transformation allows a rare gold-catalyzed dynamic deracemization of chiral racemic substrates, where the same catalyst is responsible for several synergistic tasks in solution. The products are useful building blocks in synthesis and enable expeditious access to natural products.

Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been develop