Catalytic Enantioselective Hydrogenation of N-Alkoxycarbonyl Hydrazones: A Practical Synthesis of Chiral Hydrazines

An enantioselective hydrogenation of hydrazones catalyzed by Rh complexes (Rh-Josiphos or Rh-Taniaphos) has been developed. The protocol can be applied to hydrazones with three different protective groups (Boc, Cbz, and methoxycarbonyl), allowing for selective deprotection and further elaboration of...

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Bibliographic Details
Published in:Organic letters 2010-01, Vol.12 (2), p.276-279
Main Authors: Yoshikawa, Naoki, Tan, Lushi, McWilliams, J. Christopher, Ramasamy, Deepa, Sheppard, Ruth
Format: Article
Language:English
Subjects:
Catalysis
Hydrazines - chemical synthesis
Hydrazines - chemistry
Hydrogenation
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
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Summary:An enantioselective hydrogenation of hydrazones catalyzed by Rh complexes (Rh-Josiphos or Rh-Taniaphos) has been developed. The protocol can be applied to hydrazones with three different protective groups (Boc, Cbz, and methoxycarbonyl), allowing for selective deprotection and further elaboration of the hydrazine products in the presence of other functional groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902602c