Communication
Asymmetric Synthesis of Chiral 1,3-Diaminopropanols: Bisoxazolidine-Catalyzed CC Bond Formation with α-Keto Amides†
Hanhui Xu,
Prof. Dr. Christian Wolf,
Hanhui Xu
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Christian Wolf
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)Search for more papers by this authorHanhui Xu,
Prof. Dr. Christian Wolf,
Hanhui Xu
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Christian Wolf
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057 (USA)Search for more papers by this author†
Funding from the National Science Foundation (CHE-0848301) is gratefully acknowledged.
Graphical Abstract
Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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