554450-38-3

Upstream product

• 89156-12-7 (1S)-(+)-10-(phenylsulfonyl)isoborneol 
• 598-21-0 2-Bromoacetyl bromide 
• 752975-96-5 ((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid 
• 591-51-5 phenyllithium 
• 41348-33-8 (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 554450-42-9 10-phenylsulfonylisobornyl 3-oxo-3-phenyl-2-triphenylphosphoranylidenepropanoate 
• 554450-43-0 10-phenylsulfonylisobornyl 3-azido-2-bromo-3-phenylpropenoate 
• 554450-39-4 (1S)-10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetate 
• 835869-68-6 (1S)-(-)-10-(phenylsulfonyl)isobornyl buta-2,3-dienoate 

Relevant academic research and scientific papers

Novel asymmetric Wittig reaction: Synthesis of chiral allenic esters

Wittig reactions between 10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetates (1 and 6) and ketenes resulted in asymmetric induction, with the selective synthesis of allenes with axial chirality. Use of the (1R)-(-)-10-(phenyl-sulfonyl)isoborneol unit allows the synthesis of allenes with S configuration, whereas use of the (1S)-(+)-10-(phenylsulfonyl)isoborneol unit produces allenes with R configuration. The structure of (1R)-(-)-10-(phenylsulfonyl)isobornyl (S)-5,5-dimethylhexa-2,3-dienoate (2e) was determined by X-ray crystallography. Chirooptical studies of the allenic esters were carried out, confirming that two sets of enantiomeric derivatives were obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral au