Work

Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties

Year: 2019

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.8b03068

Authors: Christopher R. Shugrue, Bianca R. Sculimbrene, Elizabeth R. Jarvo, Brandon Q. Mercado, Scott J. Miller

Institution: Yale University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institute of General Medical Sciences, Division of Graduate Education

Awards: G1775311264, G2991418009, Selective Peptide-Based Oxidation Catalysts for Bioactive Molecule Synthesis