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Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters.

ABSTRACT: A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3985890 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters.

Trost Barry M BM Miege Frédéric F

Journal of the American Chemical Society 20140213 8

A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity. ...[more]

PMID: 24502188

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