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Asymmetric Diels-Alder reaction: Cis-1-arylsulfonamido-2-indanols as highly effective chiral auxiliaries

✍ Scribed by Arun K. Ghosh; Packiarajan Mathivanan


Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
236 KB
Volume
7
Category
Article
ISSN
0957-4166

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✦ Synopsis


Lewis acid promoted Diels-Alder reaction of acrylate esters of -1-arylsulfonamido-2-indanols and cyclopentadiene provided exclusively -adducts with high -diastereoselectivities.


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The use ofa mono-pivalate mono-acrylate bis-ester of (+)-lS,5S,6S-spirol4.4]nonane-l,6diol in an asymmetric Dieis-Alder reaction with cyclopentadiene (2 equiv. BCI3, -85Β°C, CH2C12) provided the expected endo bicyclo adduct in >97% de. Iodolactonization of the bicyclo adduct provided the (+)-lactune