209852-87-9

Basic information

• Product Name: 8-Oxabicyclo[3.2.1]oct-6-en-3-one, 2-[(1S)-1-phenylethoxy]-, (1R,2S,5R)-
• CAS NO: 209852-87-9
• Molecular Formula: C15H16O3
• Molecular Weight: 244.29
• Mol File: 209852-87-9.mol

Chemical Properties

• CAS DataBase Reference: 8-Oxabicyclo[3.2.1]oct-6-en-3-one, 2-[(1S)-1-phenylethoxy]-, (1R,2S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Oxabicyclo[3.2.1]oct-6-en-3-one, 2-[(1S)-1-phenylethoxy]-, (1R,2S,5R)-(209852-87-9)
• EPA Substance Registry System: 8-Oxabicyclo[3.2.1]oct-6-en-3-one, 2-[(1S)-1-phenylethoxy]-, (1R,2S,5R)-(209852-87-9)

Safety Data

• Hazardous Substances Data: 209852-87-9(Hazardous Substances Data)

Upstream product

• 110-00-9 furan 
• 875545-07-6 (S)-[1-Methoxy-1-(1-phenylethoxy)methylvinyloxy]triethylsilane 

Downstream Products

• 403666-62-6 (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate 
• 403666-31-9 (1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate 
• 403666-32-0 (1'S,1R,2R,3R,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate 
• 403666-53-5 (1'S,1R,2S,4S,5S)-(2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one-4-yl) pivaloate 
• 403666-30-8 (1'S,1R,2S,4R,5S)-(2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]octa-6-ene-3-one-4-yl) pivaloate 
• 403666-52-4 (1'S,1R,2S,5S)-4-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 875545-09-8 (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene 
• 905984-03-4 (1S,2S,4S,5R)-2-fluoro-4-((S)-1-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 905984-04-5 (1S,2S,4S,5R)-2-fluoro-4-acetoxy-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 403666-51-3 (1'S,1R,2S,5S)-2-(1'-phenylethoxy)-3-triethylsilanyloxy-8-oxabicyclo[3.2.1]octa-3,6-diene 

Relevant articles and documents

Bicyclo[3.2.1]octanone catalysts for asymmetric alkene epoxidation: the effect of disubstitution

A series of 2-fluoro-8-oxabicyclo[3.2.1]octan-3-ones are prepared and tested as catalysts for alkene epoxidation with Oxone. These catalysts provide trans-stilbene oxide with up to 83% ee, but the highest ee value is obtained with the monofluorinated ketone 2: both 2,2- and 2,4-disubstituted catalysts afford epoxide of lower ee.

Chiral Allyl Cations Are Capture by Furan with 100% Stereoselectivity: Synthesis of Enantiopure 2-Alkoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones by Low-Temperature [4+3] Cycloaddition

A low-temperature (-95°C) protocol for intermolecular cycloadditions of furan to chiral silyloxyallyl cations in dichloromethane is described. Key precursors are open-chain, mixed α-ketoacetals, which are chiral. The resulting [4+3] cycloadducts are dense

Chiral allyl cations in cycloadditions to furan: Synthesis of 2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one in high enantiomeric purity

Efficient shielding of the π face is offered by the phenyl group of the chiral auxiliary (TES = triethylsilyl) to the allyl cation generated at low temperature from 1. This protection induces high π-facial selectivity and allows high chemical yield on the capture of the cation by furan to afford the title cycloadduct 2.