Journal
ACCOUNTS OF CHEMICAL RESEARCH
Volume 33, Issue 6, Pages 412-420Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ar990077w
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Funding
- NIGMS NIH HHS [R01-GM57034] Funding Source: Medline
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Although Lewis bases (e.g., tertiary phosphines, tertiary amines, and pyridines) serve as nucleophilic catalysts for a wide array of reactions, there have been relatively few reports of enantioselective nucleophilic catalysts. In this Account, we describe the design and synthesis of a new family of chiral nucleophilic catalysts, specifically, planar-chiral heterocycles. These complexes provide good levels of enantiomeric excess in the addition of alcohols to ketenes, the rearrangement of O-acylated azlactones, and the kinetic resolution of secondary alcohols.
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