Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 35, Pages 8764-8768Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801434
Keywords
Asymmetric catalysis; Carboxylic acids; Cyclopropanes; Organocatalysis; Strained molecules
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Funding
- Spanish MINECO [FEDER-CTQ2017-83633-P, FEDER-CTQ2016-76155-R]
- Basque Government [IT908-16]
- UPV/EHU
- Government of Aragon
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In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring-opening of formylcyclopropanes after activation of the latter through iminium ion formation. Under optimized reaction conditions, a variety of gamma-acyloxy-substituted aldehydes can be obtained in high yields and enantioselectivities through the desymmetrization of substituted meso-formylcyclopropanes in the presence of a chiral secondary amine as catalyst.
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