80868-57-1

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 73440-88-7 (+)-(1R,2S,3R,4S)-2-hydroxy-3-benzyloxy-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 80868-48-0 cis-3-benzyloxyisobornyl acrylate 
• 542-92-7 cyclopenta-1,3-diene 
• 100-44-7 benzyl chloride 

Relevant academic research and scientific papers

HIGH ASYMMETRIC INDUCTION IN DIELS-ALDER ADDITIONS OF CYCLOPENTADIENE TO ACRYLATES DERIVED FROM ISOBORNEOL

Starting from (R)-(+)- and from (S)-(-)-camphor the chiral alcohols 1, 2 and 3 have been prepared; their acrylates II underwent TiCl2(OR)2-promoted Diels-Alder additions to cyclopentadiene giving efficiently in a predictable manner either the (2R)- or the (2S)-adducts III with up to virtually quantitative asymmetric induction.

Asymmetric Induction in Diels-Alder Reactions to Acrylates Derived from Chiral sec-Alcohols

Starting from the enantiomerically pure monoterpenes (+)-pulegone (3), (+)-limonene (7), (-)-β-pinene (9), (+)- and (-)-camphor (13) or (+)-cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 and 18 were prepared; their acrylates II underwent a TiCl4-promoted Diels-Alder addition to cyclopentadiene (Scheme 3, Table) giving in a predictable manner either the (2R)- or the (2S)-adducts III with 63 to 88percent asymmetric induction.