Enantioselective organocatalytic hydride reduction - PubMed (original) (raw)
. 2005 Jan 12;127(1):32-3.
doi: 10.1021/ja043834g.
Affiliations
- PMID: 15631434
- DOI: 10.1021/ja043834g
Enantioselective organocatalytic hydride reduction
Stéphane G Ouellet et al. J Am Chem Soc. 2005.
Abstract
The first enantioselective organocatalytic hydride reduction has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of beta,beta-substituted alpha,beta-unsaturated aldehydes to generate beta-stereogenic aldehydes. The use of imidazolidinone 2 as the asymmetric catalyst has been found to mediate the transfer of hydrogen to a large class of enal substrates from ethyl Hantzsch ester. The capacity of catalyst 2 to accelerate E-Z isomerization prior to selective E-olefin reduction allows the implementation of geometrically impure enals in this operationally simple protocol.
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