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Seebach's conjunctive reagent enables double cyclizations.

ABSTRACT: When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

SUBMITTER: Chandler BD

PROVIDER: S-EPMC3230265 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Seebach's conjunctive reagent enables double cyclizations.

Chandler Brent D BD Roland Jason T JT Li Yukai Y Sorensen Erik J EJ

Organic letters 20100601 12

When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein. ...[more]

PMID: 20481611

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