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Intramolecular ene reaction of a chiral bicyclic lactam.

ABSTRACT: The preparation of bicylic lactam 2 is described, employing an acetoacetate-based synthesis of 1,4-ketoacid 3. The lactam 2 was shown to undergo a thermal ene reaction at 280-300 degrees C to afford tricycle 7. Reduction of the ene product followed by removal of the chiral auxiliary fragment provided the unusual lactam system 9 in highly enantioenriched form.

SUBMITTER: Resek JE

PROVIDER: S-EPMC2736314 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Intramolecular ene reaction of a chiral bicyclic lactam.

Resek James E JE

The Journal of organic chemistry 20081201 24

The preparation of bicylic lactam 2 is described, employing an acetoacetate-based synthesis of 1,4-ketoacid 3. The lactam 2 was shown to undergo a thermal ene reaction at 280-300 degrees C to afford tricycle 7. Reduction of the ene product followed by removal of the chiral auxiliary fragment provided the unusual lactam system 9 in highly enantioenriched form. ...[more]

PMID: 18975907

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