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J Org Chem. 2019 Feb 1;84(3):1664-1672. doi: 10.1021/acs.joc.8b03068. Epub 2019 Jan 16.

Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties.

Author information

1
Department of Chemistry , Yale University , P.O. Box 208107, New Haven , Connecticut 06520-8107 , United States.

Abstract

We herein report two examples of one-pot, simultaneous reactions, mediated by multiple, orthogonal catalysts with the same catalytic motif. First, BINOL-derived chiral phosphoric acids (CPA) and phosphothreonine (pThr)-embedded peptides were found to be matched for two different steps in double reductions of bisquinolines. Next, two π-methylhistidine (Pmh)-containing peptides catalyzed enantio- and chemoselective acylations and phosphorylations of multiple substrates in one pot. The selectivity exhibited by common reactive moieties is adjusted solely by the appended chiral scaffold through outer-sphere interactions.

PMID:
30608173
PMCID:
PMC6358474
[Available on 2020-02-01]
DOI:
10.1021/acs.joc.8b03068

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