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Methyl 3-oxobicyclo[2,2,1]heptane- and 3-oxobicyclo[2,2,2]octane-2-carboxylates: preparation and properties

✍ Scribed by Peter Chamberlain; Allison E. Rooney

Book ID
108384722
Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
195 KB
Volume
20
Category
Article
ISSN
0040-4039

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In the title compound, C 24 H 38 N 2 O 6 S 2 , which was synthesized from (+)-10-camphorsulfonic acid chloride and piperazine, the central piperazine ring adopts a chair conformation. The two camphorlsulfonyl groups are bound to the piperazine N atoms in equatorial positions. The molecule has approx

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By changing the cyclisation conditions (Nail in THF or NaOEt in EtOH), an enantiopure malonamide containing an enoate acceptor afforded either diastereomeric pyrrolidin-2-one 3 or 4 as the major product of the intramolecular conjugate addition. After separation, both diastereomers were converted thr