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Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

ABSTRACT: Dihydropyran derivatives readily undergo addition to N-acyl imines in the presence of chiral phosphoric acids. This addition process yields an attractive product that is capable of a tandem oxidative-cyclization via an epoxide intermediate.

SUBMITTER: Li G

PROVIDER: S-EPMC2863994 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Li Guilong G Kaplan Matthew J MJ Wojtas Lukasz L Antilla Jon C JC

Organic letters 20100501 9

Dihydropyran derivatives readily undergo addition to N-acyl imines in the presence of chiral phosphoric acids. This addition process yields an attractive product that is capable of a tandem oxidative-cyclization via an epoxide intermediate. ...[more]

PMID: 20361794

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