4.8 Article

Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea

Journal

ORGANIC LETTERS
Volume 12, Issue 4, Pages 708-711

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol902722y

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Funding

  1. Skaggs Institute for Chemical Biology

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Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable alpha-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active alpha,beta-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.

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