Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 49, Pages 17590-17594Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604606
Keywords
asymmetric catalysis; cyclic ketimines; Reformatsky reaction; zinc; beta-amino ester
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Funding
- MINECO (Gobierno de Espana) [CTQ2013-47494-P]
- Generalitat Valenciana
- MINECO
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A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral b-amino esters with good yields and excellent enantioselectivities is reported. A readily available diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral beta-amino esters.
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