Discrimination of Mobile Supramolecular Chirality: Acylative Molecular Transformations by Organocatalysis

by Ayumi Imayoshi

Overview

This book proposes a novel concept for molecular recognition. In the field of asymmetric synthesis approaching the mature science, asymmetric discrimination and catalytic synthesis of chiral supramolecules still stand as unsolved problems. The extreme difficulty in asymmetric synthesis of such supramolecules may result from the mobile nature of supramolecular chirality. Here the author shows the first highly enantioselective synthesis of mechanically chiral supramolecules. In the presence of a chiral organocatalyst, a mechanically planar chiral rotaxane was obtained with p erfect enantiopurity (>99% ee) with an excellent selectivity. The dynamic and flexible recognition mode enabled asymmetric synthesis of supramolecules with conformational flexibility and mobility. The recognition mode of the catalyst is a contrast to the traditional static and rigid recognition mode of the typical conventional catalysts. The concept of dynamic molecular recognition will be adopted as a novelconcept in a wide range of fields beyond the field of organic chemistry, including material chemistry, biochemistry, and medicinal chemistry.

Product Details

ISBN-13:	9789811674310
Publisher:	Springer-Verlag New York, LLC
Publication date:	11/18/2021
Series:	Springer Theses
Sold by:	Barnes & Noble
Format:	eBook
File size:	21 MB
Note:	This product may take a few minutes to download.

Table of Contents

Introduction.- Mechanistic Study of Organocatalytic Chemoselective Monoacylation of 1,5-Pentanediol.- Discrimination of Mobile Supramolecular Chirality: Kinetic Resolution of Topologically Chiral Racemic Rotaxanes by Organocatalysis.- Conclusion and Perspective.

Editorial Reviews

Reviewer: Peter J. Kennelly, PhD (Virginia Tech)
Description: This book, a volume in the Springer Theses series, presents the PhD thesis of Dr. Ayumi Imayoshi, who received her PhD from the Graduate School of Pharmaceutical Sciences at Kyoto University. The volumes in this series are unique in that, aside from a supervisor's foreword, no attempt has been made to organize the contents into a more "book-like" narrative.
Purpose: The purpose of this series is to recognize outstanding PhD research.
Audience: The primary audience would appear to be other synthetic organic chemists, in particular those interested in strategies for constructing molecules and molecular complexes of a single, defined, stereochemistry. As the biomolecules of living organisms, including the human body, are stereochemically homogeneous, the ability to generate stereochemically homogenous molecules at the bench or in an industrial reactor would be of great benefit for the production of pharmaceuticals and other therapeutics.
Features: Although lavishly illustrated with figures depicting structures and reactions, as a reprint of an academic thesis in chemistry, the book is written in the highly dense and compact style characteristic of the discipline. This style offers little room for the types of lengthy introductory material and guiding segues characteristic of works intended to be published in book form. Moreover, by its very nature, a graduate student thesis is written with a relatively narrow target audience in mind, the members of the student's thesis examination committee and colleagues working in the topic area of the thesis. Nevertheless, the quality and clarity of the writing is quite good, and hence able to ameliorate these limitations to a substantive degree.
Assessment: Many chemists will no doubt find this description of the influence of this unusual form of molecular chirality on the regioselectivity and stereochemistry of chemical reactions to be of great interest. However, while the thesis is clearly written and well illustrated, nonspecialists may struggle with the telegraphic manner in which it presents the complex story of this novel phenomenon. Nevertheless, even casual readers will no doubt agree that Dr. Imayoshi's thesis is indeed a most worthy addition to this series.

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