Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 31, Pages 12680-12683Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003886
Keywords
asymmetry; haloesterification; halogen bonding; catalysts; pi-pi stacking
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Funding
- JSPS KAKENHI [19H02709]
- [JP16H01004]
- [JP18H04237]
- [17KT0011]
- Grants-in-Aid for Scientific Research [19H02709] Funding Source: KAKEN
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Catalytic asymmetric iodoesterification of simple alkenes was achieved using a dinuclear zinc-3,3 '-(R,S,S)-bis(aminoimino)binaphthoxide (di-Zn) complex. For iodoesterification using p-methoxybenzoic acid, the N-iodonaphthalenimide (NIN)-I-2 system was effective for producing iodoesters in a highly enantioselective manner. The synthetic utility of chiral iodo-p-methoxybenzoates was also demonstrated. The quartet of metal ionic bond, hydrogen bond, halogen bond, and pi-pi stacking is harmonized on the single reaction sphere of di-Zn catalyst for enabling the highly enantioselective catalytic asymmetric iodoesterification of simple alkenes for the first time.
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