4.8 Article

Organocatalytic Activation of Inert Hydrosilane for Peptide Bond Formation

Journal

ORGANIC LETTERS
Volume 24, Issue 39, Pages 7194-7199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02947

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Funding

  1. Daiko Foundation, Japan [9226]

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We describe the development of a reliable catalytic protocol for peptide bond formation that is generally applicable to natural and unnatural alpha-amino acids, beta-amino acids, and peptides bearing various functional groups. A 10 mol % loading of HSi[OCH(CF3)(2)](3) as a catalyst was sufficient to guarantee a consistently high yield of the resulting peptide. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.
We describe the development of a reliable catalytic protocol for peptide bond formation that is generally applicable to natural and unnatural alpha-amino acids, beta-amino acids, and peptides bearing various functional groups. A 10 mol % loading of HSi[OCH(CF3)(2)](3) as a catalyst was sufficient to guarantee a consistently high yield of the resulting peptide. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.

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