Enantioselective Organocatalytic Desymmetric Acylation as an Access to Orthogonally Protected myo-Inositols

TL;DR

This paper introduces a new method to efficiently create chiral myo-inositol derivatives using an organocatalytic process.

Contribution

A metal-free, organocatalytic method for enantioselective desymmetric acylation of myo-inositol diol is presented.

Findings

The method achieves high enantioselectivity and moderate to high yields.

It is tolerant to various functional groups and scalable for practical applications.

The approach enables synthesis of orthogonally protected myo-inositol building blocks.

Abstract

Chiral cyclitols represent an important class of naturally
occurring
compounds. In particular, myo-inositol and its derivatives
are essential for phosphorus storage and cell-signaling pathways in
living organisms. Not surprisingly, these compounds constitute an
emerging class of molecules with significant potential in both medicinal
and synthetic chemistry. However, efficient catalytic methodologies
for accessing chiral myo-inositol derivatives remain
scarce. Herein, we report a metal-free, organocatalytic protocol for
the desymmetric acylation of a readily available meso-myo-inositol diol. The reaction proceeds with high
enantioselectivity, moderate to high yields, and broad tolerance to
various functional groups. The developed methodology enables the efficient
synthesis of chiral myo-inositol derivatives. Furthermore,
its scalability and subsequent transformations into orthogonally protected
building blocks for synthesizing myo-inositol phosphates
underscore the practical utility of this approach.

Figures