89156-16-1

Upstream product

• 89156-14-9 Acrylic acid (1S,2R,4R)-1-benzenesulfonylmethyl-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 89156-12-7 (1S)-(+)-10-(phenylsulfonyl)isoborneol 
• 41348-33-8 (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

PREPARATION, STRUCTURE AND ASYMMETRIC DIELS-ALDER REACTIONS OF 10-ARYLSULFONYLISOBORNYL ACRYLATES

The crystalline chiral auxiliaries 4 and 5 were readily prepared from champhorsulfonic acid.Their acrylates underwent the Diels-Alder reactions 6->7 with modest asymmetric induction consistent with an X-ray study of 6a.

Practical Asymmetric Diels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates

Starting from (+)-camphor-10-sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps.Lewis-acid-mediated -additions of their acrylates to 1,3-dienes were studied.Notably, the crystalline acrylate 4 underwent TiCl2(OiPr)2-promoted Diels-Alder addition to cyclopentaniene giving after recrystallization efficiently the pure (2R)-adduct 5.