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Yamamoto. Chem Synth 2022;2:14 Chemical Synthesis
DOI: 10.20517/cs.2022.12

Feature Article Open Access

From Lewis acids to peptide chemistry

Hisashi Yamamoto *

Peptide Research Center, Chubu University, Kasugai, Aichi 487-8501, Japan.
Correspondence to: Prof. Hisashi Yamamoto, Peptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi
487-8501, Japan. E-mail: yamamoto.hisashi@gmail.com

How to cite this article: Yamamoto H. From Lewis acids to peptide chemistry. Chem Synth 2022;2:14.
https://dx.doi.org/10.20517/cs.2022.12

Received: 17 May 2022 First Decision: 25 Jun 2022 Revised: 12 Jul 2022 Accepted: 13 Jul 2022 Published: 19 Jul 2022
Academic Editor: Bao-Lian Su Copy Editor: Peng-Juan Wen Production Editor: Peng-Juan Wen

Keywords: Peptides, protection free, non-racemization

INTRODUCTION
Despite the importance of peptide synthesis in medicinal chemistry, the current organic synthetic methods
for peptides were developed almost 50 years ago. Completely new synthetic methodologies are therefore
clearly necessary for modern organic synthesis. This article summarizes several new aspects in this regard
from our laboratory.

In the 1970s, we initiated research into Lewis acids, an amazing area of organic chemistry. Lewis acids
coordinate to various functional groups in substrates. After coordination, the reactivity of the functional
group changes significantly. This new chemistry of Lewis acid catalysts opened a new door for initiating
numerous new reactions for organic synthesis. For example, after coordination by a Lewis acid, the carbonyl
group reactivity changes completely . We have published numerous studies and revealed several leading
[1]
[2]
principles of these new reactions . However, the changes in reactivity are only for one functional group of a
given substrate. This chemistry is known as a “reagent-controlled” or “catalyst-controlled” reaction. In fact,
most of the organic reactions known to humans originate from reagent-controlled reactions. In contrast,
most biological reactions in the human body proceed through multiple functional groups of the same
substrate. This multi-functional interaction is known as a “substrate-controlled” reaction. We are interested
in substrate-controlled reactions and have reported a number of reactions, including the asymmetric
epoxidation of olefinic alcohols .
[3,4]

© The Author(s) 2022. Open Access This article is licensed under a Creative Commons Attribution 4.0
International License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, sharing,
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