Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 7, Pages 1646-1648Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801804
Keywords
Diastereoselectivity; Boron; Nucleophilic addition; Chiral auxiliaries
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Funding
- Howard Hughes Medical Institute
- National Center for Research Resources from the NIH [5 P20 RR016461]
- National Institute of General Medical Sciences from the NIH [8 P20 GM103499]
- College of Charleston School of Science and Math Dean's Research Fund
- National Science Foundation [1429308]
- College of Charleston
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Benzylation reactions of N-tosylimines and N-tert-butanesulfinyl imines using benzylboronic acid pinacol ester are reported. s-Butyllithium was used to activate the boronic ester, rendering it nucleophilic. The reaction was compatible with electronically diverse substituents on the imine in both substrate classes. Good diastereoselectivity was observed in additions to N-tert-butylsulfinylaldimines. The diastereoselectivity observed in these reactions is consistent with an open transition state for the addition. Examples of a secondary alkylboronic ester nucleophile and a N-tert-butanesulfinyl trifluoromethylketimine electrophile are also included.
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