Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.
Org Lett
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| Abstract | Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps. |
| Year of Publication | 2006
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| Journal | Org Lett
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| Volume | 8
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| Issue | 18
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| Pages | 3999-4002
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| Date Published | 2006 Aug 31
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| ISSN | 1523-7060
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| URL | |
| DOI | 10.1021/ol061473z
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| PubMed ID | 16928058
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