Abstract
An enantioselective α-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting α,β-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alcohols / chemistry*
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Aldehydes / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Catalysis
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Combinatorial Chemistry Techniques
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Esters
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Ketones / chemical synthesis
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Ketones / chemistry*
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Lactones / chemical synthesis
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Lactones / chemistry
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Molecular Structure
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Pyrroles / chemistry*
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Stereoisomerism
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Zinc / chemistry*
Substances
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Alcohols
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Aldehydes
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Bridged Bicyclo Compounds, Heterocyclic
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Esters
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Ketones
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Lactones
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Pyrroles
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peloruside A
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3-hydroxybutanal
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Zinc