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

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 ?-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.

SUBMITTER: Shugrue CR

PROVIDER: S-EPMC6358474 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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

Shugrue Christopher R CR Sculimbrene Bianca R BR Jarvo Elizabeth R ER Mercado Brandon Q BQ Miller Scott J SJ

The Journal of organic chemistry 20190116 3

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 ...[more]

PMID: 30608173

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