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Diastereo- and enantioselective additions of ?-nitro esters to imines for anti-?,?-diamino acid synthesis with ?-alkyl-substitution.

ABSTRACT: The discovery that a C2-symmetric bis(AMidine) [BAM] catalyst promotes an anti-selective addition of ?-substituted ?-nitro esters to imines is described, providing ?-substituted ?,?-diamino ester products with high diastereo- and enantioselectivity. When compared to the function of a BAM catalyst reported previously, the pair offer a rare example of diastereodivergence using a bifunctional Brønsted acid-base organocatalyst.

SUBMITTER: Sprague DJ

PROVIDER: S-EPMC5903423 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution.

Sprague Daniel J DJ Singh Anand A Johnston Jeffrey N JN

Chemical science 20180131 8

The discovery that a C2-symmetric bis(AMidine) [BAM] catalyst promotes an anti-selective addition of α-substituted α-nitro esters to imines is described, providing α-substituted α,β-diamino ester products with high diastereo- and enantioselectivity. When compared to the function of a BAM catalyst reported previously, the pair offer a rare example of diastereodivergence using a bifunctional Brønsted acid-base organocatalyst. ...[more]

PMID: 29719706

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