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Synthesis and Diels-Alder reactions of t-butyl and t-butyl, methyl (S)s-2-p-tolylsulfinylmaleates, chiral synthetic equivalents of monoalkyl and mixed dialkyl acetylenedicarboxylates

✍ Scribed by Inés Alonso; J.Carlos Carretero; José L. García Ruano


Book ID
104225125
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
298 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis


The reaction of t-butyl p-tolylsulfinylacetate with glyoxyltc acid yielded maleate monoester 1, whose methylat!on afforded asymmetrlc dlester 2. Conditions in which 1 and 2 react with cyclopentadiene exhibiting htgh faoal and endo selectlvities are reported. 3.-See for example. a) P.


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Chiral dienophiles l-3 undergo highly exo and diasfereoface selective Die/s-Alder reactions. The Die/s-Alder reactions of 3 are also highly exo selective under Lewis acid catalyzed conditions. In connection with an ongoing effort in the natural products arena we required a highly diastereoselective