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Title: Enantio- And Diastereoselective Double Mannich Reaction between Ketones and Imines Catalyzed by Zn-ProPhenol
Authors: Trost B.M.
Gnanamani, Elumalai
Published in: Organic Letters
Abstract: Herein we present a Zn-ProPhenol-catalyzed double Mannich reaction between ynones and imines that generates 1,3-diamines in excellent yield as well as diastereo- and enantioselectivity (>99.5% ee). With 2.2 equiv of a single imine electrophile, we obtain pseudo-symmetrical diamines whereas, with two different imine partners, we obtain unsymmetrically substituted 1,3-diamines with three contiguous stereocenters. In addition, we showcase the utility of these double Mannich adducts by transforming the 1,3-diamine motif into a variety of interesting products. Copyright © 2020 American Chemical Society.
Citation: Organic Letters (2020), 22(4): 1675-1680
Issue Date: 2020
Publisher: American Chemical Society
ISSN: 15237060
Author Scopus IDs: 57217139833
Author Affiliations: Trost, B.M., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Gnanamani, E., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Funding Details: We thank Dr. Jana Maclaren and Rebecca Winslow Smaha (Stanford Nano Shared facilities, Stanford University) for X-ray crystallographic analysis. We also thank Dr. Christopher A. Kalnmals and Dr. Jacob S. Tracy (Department of Chemistry, Stanford University) for technical assistance. We thank the Tamaki Foundation and Chugai pharmaceuticals for financial support.
Corresponding Author: Trost, B.M.; Department of Chemistry, Stanford UniversityUnited States; email:
Appears in Collections:Journal Publications [CY]

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