Publication: Ring-to-thread chirality transfer in [2]rotaxanes for the synthesis of enantioenriched lactams
Date
2022-09-19
Authors
Lopez-Leonardo, Carmen ; Saura Sanmartín, Adrián ; Marin-Luna, Marta ; Alajarín, Mateo ; Martinez-Cuezva, Alberto ; Berna, Jose
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Martinez-Cuezva, Alberto ; Berna, José
Publisher
Wiley-VCH
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DOI
https://doi.org/10.1002/anie.202209904
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info:eu-repo/semantics/article
Description
© 2022, The Authors. This manuscript version is made available under the CC-BY-NC 4.0 license https://creativecommons.org/licenses/by-nc/4.0/
This document is the Published version of a Published Work that appeared in final form in Angewandte Chemie International Edition. To access the final edited and published work see https://doi.org/10.1002/anie.202209904
Abstract
The synthesis of chiral mechanically interlocked molecules has attracted a lot of attention in the last few years, with applications in different fields, such as asymmetric catalysis or sensing. Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows enantioenriched value-added compounds, such as lactams of different ring sizes and amino acids, to be obtained. The chiral information is effectively transmitted across the mechanical bond from the encircling ring to the interlocked lactam. High levels of enantioselectivity and full control of the regioselectivity of the final cyclic compounds are attained.
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Citation
Angewandte Chemie International Edition, 61, 39, 2022, e202209904
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