88708-22-9

Upstream product

• 134297-24-8 (1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide 
• 79902-01-5 2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile 
• 134297-23-7 (1R,4R,5R)-5-((R)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-2-ene 
• 88764-13-0 (1R,2R,4R)-2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl(1S)-camphanate 

Downstream Products

• 128573-16-0 (-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one 
• 115880-18-7 N-(1-phenylethyl)-7-oxabicyclo<2.2.1>hept-5-en-2-ylimine 
• 115880-18-7 N-(1-phenylethyl)-7-oxabicyclo<2.2.1>hept-5-en-2-ylimine 
• 136057-85-7 C₂₁H₃₁⁽²⁾HO₅SSi 
• 136057-86-8 [(1S,3S,6R,7S,9R)-9-Allyl-5-(2-benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane 
• 136057-82-4 [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Synthesis of 2,6-dioxabicyclo[3.3.0]octenes by tandem ring-rearrangement/cross metathesis

A facile synthesis of stereodefined 2,6-dioxabicyclo[3.3.0]octene derivatives from the vinyl ether of endo-7-oxanorbornen-2-ol via tandem ring-opening/ring-closing(ring-rearrangement)/cross metathesis is reported.

Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

p-Tolyl vinyl sulfoxide has been efficiently activated for the Diles-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf.Very high diastereomeric excesses have been achieved (>98percent) at -20 deg C in many cases.Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene.In this way enantiomerically pure oxanorbornenone 19a has been prepared.The reaction mechanism is briefly discussed.

Optical Resolution of 7-Oxabicyclohept-2-ene Derivatives. Diastereoselectivity in the Formation of Cyanohydrine-Brucine Complexes

A new, practical method for the optical resolution of bicyclic ketones is illustrated by the preparation of (+)-(1R,4R)-7-oxabicyclohept-5-en-2-one ((+)-1) and (+)-(1R,2S,4R)-2-cyano-7-oxabicyclohept-5-en-2-yl acetate ((+)-4).It involves the diastereoselective formation of a brucine complex with the corresponding cyanhydrine mixture.

182. The Preparation of Optically Pure 7-Oxabicyclohept-2-ene Derivatives. The CD Spectrum of (+)-(1R)-7-Oxabicyclohept-5-en-2-one

(-)-1-Camphanoyloxyacrylonitrile (=(-)-1-cyanovinyl camphanate; 1) obtained from the commercially available (-)-camphanoyl chloride and 2-oxopropiononitrile added to furan at 20 deg C in the presence of Cu(BF4)2*6H2O or ZnI2 and gave a mixture of 2-cyano-