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Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction.

ABSTRACT: Enantiomerically pure ?-aminoalcohols, produced through an organocatalytic Mannich reaction, were subjected to an Ugi multicomponent reaction under classical or Lewis acid-promoted conditions with diastereoselectivities ranging from moderate to good. This approach represents a step-economical path to enantiomerically pure, polyfunctionalized peptidomimetics endowed with three stereogenic centers, allowing the introduction of five diversity inputs.

SUBMITTER: Caputo S

PROVIDER: S-EPMC4734417 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction.

Caputo Samantha S Basso Andrea A Moni Lisa L Riva Renata R Rocca Valeria V Banfi Luca L

Beilstein journal of organic chemistry 20160126

Enantiomerically pure β-aminoalcohols, produced through an organocatalytic Mannich reaction, were subjected to an Ugi multicomponent reaction under classical or Lewis acid-promoted conditions with diastereoselectivities ranging from moderate to good. This approach represents a step-economical path to enantiomerically pure, polyfunctionalized peptidomimetics endowed with three stereogenic centers, allowing the introduction of five diversity inputs. ...[more]

PMID: 26877816

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