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Synthesis of bicyclic γ-lactones promoted by Mn(OAc)3: Regio- and diastereoselectivities

✍ Scribed by Laurent Lamarque; Alain Méou; Pierre Brun


Book ID
104208584
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
471 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


The regio-and diastereoselectivities of Mn(OAc)3-induced addition of monomethyl malonate on some cvcloalkenes and cycloalkaa~enes are studied The latter is great(v improved when starting .from cvcloalkadienes.


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The acid-catalyzed ring opening of the title epoxide 1 takes place at the C-l atom with retention of configuration at C-2 to form 2,3-cis-2-hydroxy-substituted y-lactol deriva= tives 3 In basic media, nucleophiles attack the C-Atom with inversion of configuration yielding 2,3-trans-lactols 5. Oxidat