108885-08-1

Upstream product

• 6994-93-0 ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride 
• 108-95-2 phenol 
• 21286-54-4 Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 220049-46-7 ((1S,4S)-7,7-Dimethyl-2,3-dioxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid phenyl ester 
• 1021299-41-1 phenyl (1S,2S,4R)-2-endo-hydroxybornane-10-sulfonate 
• 41348-33-8 (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 247078-63-3 (1S,2R)-(7,7-dimethyl-2-hydroxybicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester 
• 220049-53-6 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-phenyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-52-5 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-propyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-51-4 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-methyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-50-3 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-styryl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-49-0 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-pent-1-enyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-48-9 [(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((E)-propenyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester 
• 220049-47-8 ((1S,2S,3R,4S)-2,3-Dihydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid phenyl ester 
• 937-41-7 phenyl acrylate 
• 247078-55-3 (1R,2R)-(7,7-dimethyl-2-exo-benzylselenylbicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester 
• 247078-53-1 (1S,2R)-(7,7-dimethyl-2-exo-phenylsulfanylbicyclo[2.2.1]hept-1-yl) methane sulfonic acid phenyl ester 

Relevant academic research and scientific papers

Stereocontrolled synthesis of novel enantiomerically pure sulfides and selenides from (+)-camphor and (+)-camphor-10-sulfonyl chloride

Synthetic approaches to novel enantiomerically pure sulfides and selenides derived from (+)-camphor and (+)-camphor-10-sulfonate esters are described. Lewis acid mediated hemiacetal formation between a camphor- derived ketone and a thiol or selenol, and subsequent in situ reduction using triethylsilane selectively gives the exo-sulfide or -selenide in moderate overall yields. The initial sulfonate ester products can be converted into the corresponding sulfones by subsequent treatment with Grignard or organolithium reagents.

Synthesis of phenyl 2-acryloyloxybornane-10-sulfonate diastereomers

Several routes to phenyl 2-exo- and 2-endo-acryloyloxybornane-10-sulfonate have been investigated. Preparation of the former product is complicated by concomitant formation of 10-isobornylsultone, while addition of HCl is observed when the alcohol precursors are treated with acryloyl chloride in the presence of Al2O3. An X-ray crystal structure has been determined for one of the chlorinated derivatives.

Diastereoselective cyclopropanation of α,β-unsaturated acetals of a novel camphor-derived chiral auxiliary

Reaction of selected α,β-unsaturated aldehydes with phenyl 2,3-dihydroxybornane-10-sulfonate affords acetals which undergo diastereoselective (> 99% de) Simmons-Smith cyclopropanation.