Calcium(II)-catalyzed enantioselective conjugate additions of amines

Brice E. Uno, Rachel D. Dicken, Louis R. Redfern, Charlotte M. Stern, Greg G. Krzywicki, Karl A. Scheidt

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The direct enantioselective chiral calcium(ii)·phosphate complex (Ca[CPA]2)-catalyzed conjugate addition of unprotected alkyl amines to maleimides was developed. This mild catalytic system represents a significant advance towards the general convergent asymmetric amination of α,β-unsaturated electrophiles, providing medicinally relevant chiral aminosuccinimide products in high yields and enantioselectivities. Furthermore, the catalyst can be reused directly from a previously chromatographed reaction and still maintain both high yield and selectivity.

Original languageEnglish (US)
Pages (from-to)1634-1639
Number of pages6
JournalChemical Science
Volume9
Issue number6
DOIs
StatePublished - 2018

ASJC Scopus subject areas

  • Chemistry(all)

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    Uno, B. E., Dicken, R. D., Redfern, L. R., Stern, C. M., Krzywicki, G. G., & Scheidt, K. A. (2018). Calcium(II)-catalyzed enantioselective conjugate additions of amines. Chemical Science, 9(6), 1634-1639. https://doi.org/10.1039/c7sc05205g