TheHelping you react with chemical reactions

Issue

6December
2021

Mirror-image molecules?

How chiral molecules
and asymmetriccatalysts interactMirror-image molecules?

How chiral molecules
and asymmetriccatalysts interact

LIST, BenjaminPrincipal Investigator

ICReDD Prinicipal Investigator and Specially Appointed Professor Benjamin List received
the 2021 Nobel Prize in Chemistry. ICReDD’s philosophy of “aiming to create a new wayof discovering chemical reactions by utilizing the strengths of researchers from differentfields” resonated strongly with Professor List, and he has been involved in ICReDD’splanning and activities as a Prinicipal Investigator since ICReDD was established.
In the 5th issue of The CATALYST, we learned about catalysts, and in this issue we willlearn about a topic related to Professor List’s prize-winning research on asymmetricorganic catalysis. Specifically, we will learn what “asymmetric” means in the world ofchemistry and how it is related to catalysts.

1. Your Reflection in the Mirror
Chances are you’ve probably
looked at yourself in themirror before. Have you evernoticed anything weird whenlooking at your reflections?
Like that the writing on yourT-shirt looks backwards inthe mirror, or that when you
hold your right hand to amirror, the reflection looks
like your left hand? Wellthat’s because a mirror
image is distinct anddifferent from the original
object. The two cannot be
placed in a way that they
perfectly overlap in thesame orientation.

3. Controlling Chemical Reflections
One of the big challenges inchemistry is that reactions
often produce both mirror
images versions of amolecule! Solving thisproblem is very important fordeveloping new medicines, as
our bodies can be very picky
about which mirror image they
will interact nicely with.
Including the wrong mirror
image in a medicine can makeit less effective, or even havethe opposite effect andactually cause harm! In ourlast issue, we talked aboutcatalysts, and a special type ofcatalyst, called an asymmetriccatalyst, can guide a reaction
so that it produces only one of
the mirror images.

2. Molecular Reflections
The same goes for molecules when theylook in the mirror. They see a different
version of themselves, where theirarrangement in 3D space is reversed,
like the letters on your T-shirt.
Molecules that are mirror images ofeach other but cannot be placed so thatthey perfectly overlap in the sameorientation are called chiral molecules.
All of their atoms and bonds are thesame, so they mostly have the same
physical properties, like their melting orboiling point. However, the different
relative arrangement of the atoms andbonds in 3D space can cause eachmirror image version of a molecule toreact differently with other molecules.
This can have some very importantconsequences.

4. State - of - the - Art Control
It was thought that asymmetric catalysts
had to have metal in them, but
Professor List developed an organic
type of these catalysts that do notcontain metal and are cheaper andmore friendly to the environment.
Researchers at ICReDD are exploring
the frontiers of what organic asymmetriccatalysts can do, so that more reactions
can be carried out with these greener
catalysts. This includes ICReDD using
machine learning and an advanced
calculation method called AFIR torationally design more complex
catalysts than previously possible,opening up even more possibilities.
With more advanced catalysts that canproduce only one of the mirror image
molecules, we can discover even morereactions that could lead to newmedicines.

on!
it
av
it
Ac
Quiz
Chiral molecules aremolecules that arealmost the same, exceptthat they have different_______________.
Send us your answer!

A Atoms
B 3D arrangements
C Bonds
D Melting Points

Check ourInstagram
highlights forthe answer
to the quiz!
#ReactWithUs@ICReDDconnectNew Researchers

ICReDDN e ws

M engf ei W a ng

Yong Z heng

Photochemical reactions

Physical properties ofsoft materials

Dennis ChungYang Huang
Transition metal catalysts
and photo-responsivematerials

December 2021

Selected Publications( from September 2021 to November 2021)
An Elastic Metal–Organic
Crystal with a Densely
Catenated Backbone(J. Pirillo, Y. Hijikata)
DOI: 10.1038/s41586-021-03880-x

Confinement-Controlled,
Either syn- or anti-Selective
Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes

Carboxylation of a Palladacycle Formed via C(sp 3 )–H
Activation: Theory-Driven
Reaction Design

Mechanochemical Synthesis ofMagnesium-Based Carbon
Nucleophiles in Air and their
Use in Organic Synthesis(Y. Harabuchi, H. Takano, H. Hayashi,(A. Hu, Y. Pang, S. Maeda, K. Kubota, H. Ito)

(N. Tsuji, B. List)

S. Maeda, T. Mita)

DOI: 10.1021/jacs.1c07447

DOI:10.1002/asia.202100989

Symposia ( invited and more)・Science Agora 2021, “New Science:
Cutting-edge Research Made Possible
by Information Science, AI, and Big Data”(M. Tsuda, L. Wang, S. Tanaka)
DOI: 10.1038/s41586-021-04266-9

DOI: 10.1038/s41467-021-26962-w

Awards・Best Poster Award, The 7th Hokkaido
University Cross-Departmental
Symposium (H. Hayashi)(I. Takigawa)

Enhanced Fusogenicity andPathogenicity of SARS-CoV-2
Delta P681R Mutation

・Nobel Prize in Chemistry 2021 (B. List)

Outreach・Monthly news postcards
・Quarterly news poster
The CATALYST 5th issue〈Co-organized Symposium〉
・ICReDD-Hokkaido University Facultyof Medicine Joint Symposium・The 7th Hokkaido University
Cross-Departmental Symposium

ICReDD-Hokkaido University Faculty ofMedicine Joint Symposium
LIST, BenjaminPrincipal Investigator

A press conference was held at
ICReDD the day after the Nobel Prizein Chemistry was announced.

Monthly news postcards

The CATALYST
5th issue

Researcher Profile

vol.6

NobuyaTsuji
Assistant Professor Tsuji develops
asymmetric chemical reactions
that utilize organic acid catalysts
and uses computational chemistry to analyze reaction mechanisms. In particular he researches
reactions that asymmetricallyactivate low reactivity functionalgroups such as alkenes.
Representative Papers:
JACS, 2021, 143, 14475–14481; JACS,2021, 143, 675–680; Science, 2018, 359,1501

Short Biography
I C R e D D Sp e c ially Appoint ed Assist ant
Pr o f e s s o r an d L ist Group Co-PI . Her e c e iv e d h is Mast ers in 201 4 from t heK y o t o U n iv e r s it y Grad uat e S c hool of
Ph ar m ac e u tic a l S c ienc es and his PhD
in 2 0 1 8 f r o m t h e M ax Planc k I nst it utf ü r K o h le n f o r s c h ung. I n 201 9, hec o m p le t e d p o s t d oc t oral researc h at
U n iv e r s it y o f C a lifornia-Berkeley andth e n s tar te d h is c urrent posit ion in
J an u ar y 2 0 2 0 .

About ICReDD
The development of new chemical reactions is intrinsically entangled with the prosperity ofhumanity and the preservation of the environment. A recent example of such transformative chemical reactions with profound impact is cross-coupling reactions, the discovery of which was awarded
with the 2010 Nobel Prize in Chemistry. These reactions are used to produce approximately 20% of
all medicinal reagents, and almost all liquid crystalline and organic electroluminescent materials.
The industrial use of these chemical reactions contributes ~60 trillion yen per annum to the global
economy. The development of new chemical reactions thus significantly affects the evolution ofsociety.
ICReDD is the Institute for Chemical Reaction Design and Discovery, a WPI center at Hokkaido
University where researchers from different disciplines combine their strengths to take full control
over chemical reactions. The institute was born out of the realization that the purposeful design ofchemical reactions requires cross-sectional collaborations at every step. Working on such a fundamental natural process, quantum-chemical computations, information technology, modern experimental techniques, and the development of advanced materials can no longer be separate fields if
we want to achieve significant breakthroughs. Rather, they have to become part of a diverse
toolbox for truly integrated research.

The Catalyst is inspired by catalysts used inchemistry to bring molecules together, to reduce
reaction barriers, and to activate molecules—to makereactions happen faster. In this spirit, this poster series
should enable its readers to make the connection
between chemical reactions and the wellbeing of oursociety, and to look at the world in a new way, seeing
how chemical reactions and chemistry shape the world
around them. And if we can take this opportunity tointroduce ourselves, too, this may also catalyze newfriendships and opportunities. #ReactWithUs

React With Us!
To stay up to datewith what’s happening at ICReDD,
follow us on our social media channels:@ICReDDconnect

We had the honor of congratulating Professor List over zoom on being awarded
the Nobel Prize in Chemistry. Sending all of our best wishes from Sapporo!

Published in December 2021
Published by theInstitute for Chemical Reaction Design and Discovery (WPI-ICReDD)
Hokkaido University
North 21, West 10, Kita Ward, Sapporo, Hokkaido, 001-0021 Japan
Telephone: + 81-11-706 -9646 (Public Relations)
Email address: public_relations@icredd.hokudai.ac.jp

https://www.icredd.hokudai.ac.jp/