214599-31-2

Upstream product

• 78622-29-4 (1S,4R)-1-(iodomethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one 
• 108-98-5 thiophenol 
• 21286-54-4 Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 745801-33-6 (1S,4R)-1-phenylsulfanylmethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one oxime 
• 214599-33-4 (2R-exo)-2-[(E)-dichloroethenoxy]-10-(phenylthio)bornane 
• 188017-81-4 (2R)-10-(phenylthio)isoborneol 

Relevant academic research and scientific papers

Development of new camphor based N,S chiral ligands and their application in transfer hydrogenation

A new class of N,S-containing chiral compounds based on the camphor scaffold have been synthesised and evaluated as chiral catalysts in the transfer hydrogenation of acetophenone. The best results were achieved using compound 6a as the ligand and [Ir(COD)Cl]2 as the metal precursor.

Camphor-derived, chelating auxiliaries for the highly diastereoselective intermolecular Pauson-Khand reaction: Experimental and computational studies

A family of enantiomerically pure (2R)-10-(alkylthio)isoborneols [methylthio (1), neopentylthio (2), phenylthio (3)], specifically designed as chiral auxiliaries suitable for chirality transfer to cobalt in Pauson-Khand reactions, has been synthesized. The dicobalt hexacarbonyl complexes of the alkoxyacetylenes derived from these alcohols (10a-12a) can be converted to the rather stable, internally chelated, pentacarbonyl complexes lOb-12b by treatment with NMO. The intermolecular Pauson-Khand reactions of 10b-12b with strained olefins take place with synthetically useful rates at low temperatures (down to -20 °C), with high yields and diastereoselectivities: norbornene (77%; 92:8), norbornadiene (82%; 96:4), bicyclo[3.2.0]hept-6-ene (91%; 93:7). The major diastereomer of the adduct of lOb with norbornadiene, 14, has been used as the starting point for a synthesis of (S)-(-)-4-alkyl-2-cyclopentenones through a se'quence consisting of completely diastereoselective conjugate addition, reductive cleavage with recovery (>95%) of the chiral auxiliary, and retro Diels-Alder reaction. The stereochemical course of the reaction of 10b with norbornadiene has been analyzed and rationalized by theoretical means by using a combined semiempirical [PM3-(tm)/density functional theory [VWN-Perdew-Wang 91] approach.