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Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

ABSTRACT: Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.

SUBMITTER: Larson SE

PROVIDER: S-EPMC2780433 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

Larson Shawn E SE Baso Juan C JC Li Guilong G Antilla Jon C JC

Organic letters 20091101 22

Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction. ...[more]

PMID: 19905027

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