194735-91-6

Basic information

• Product Name: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1alpha,5beta,6alpha)-(9CI)
• Synonyms: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1alpha,5beta,6alpha)-(9CI)
• CAS NO: 194735-91-6
• Molecular Formula: C8H12O3
• Molecular Weight: 0
• Product Categories: CARBOXYLICESTER
• Mol File: 194735-91-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1alpha,5beta,6alpha)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1alpha,5beta,6alpha)-(9CI)(194735-91-6)
• EPA Substance Registry System: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1alpha,5beta,6alpha)-(9CI)(194735-91-6)

Safety Data

• Hazardous Substances Data: 194735-91-6(Hazardous Substances Data)

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 99418-15-2 2-oxabicyclo[3.1.0]hexane-6-carboxylic acid 
• 104036-66-0 (2-ethoxy-tetrahydro-[3]furyl)-acetic acid ethyl ester 
• 90113-46-5 ethyl 2-(tetrahydrofuran-3-yl)acetate 

Relevant articles and documents

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Highly Enantioselective Intermolecular Cu(I)-Catalyzed Cyclopropanation of Cyclic Enol Ethers. Asymmetric Total Synthesis of (+)-Quebrachamine

A set of cyclic enol ethers derived from 2,3-dihydrofuran 35 and 3,4-dihydropyran 8 with a varying substitution pattern at the olefinic system were synthesized. Evans's ligand 5 with Cu(I)OTf was found to be an effective catalyst in the cyclopropanation reaction between cyclic enol ethers 14, 19, 28-31, and 33 and ethyl diazoacetate 6 to give diastereoselectivities up to exo/endo = 95:5 and enantioselectivities higher than 95% in nearly all cases. Because of the selective building of a quarternary carbon center and good yields in the formation of bicyclic structures 34c-h, the reaction was used as a key step in the asymmetric synthesis of (+)-quebrachamine 7, an indole alkaloid of the Aspidosperma family. After acid-induced ring opening of bicyclic compound 34f to lactone 40 followed by LiAlH4 reduction to the masked aldehyde 41, a reaction with tryptamine gave intermediate 42. This alcohol was efficiently converted into the indole alkaloid (+)-quebrachamine 7 in an overall yield of 37% starting from the chiral synthon 34f. Moreover it revealed the absolute configuration of the quarternary center of the cyclopropanation product 34f to be S.

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Keywords: carbene complexes; chromium; cyclopropanations; homogeneous catalysis