Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols

Carla Alamillo-ferrer; Christian D.-t. Nielsen; Andrea Salzano; Xavier Companyó; Riccardo Di Sanza; Alan C. Spivey; Henry S. Rzepa; Jordi Burés

doi:10.1021/acs.joc.0c02998

Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols

Carla Alamillo-ferrer, Christian D.-t. Nielsen, Andrea Salzano, Xavier Companyó, Riccardo Di Sanza, Alan C. Spivey, Henry S. Rzepa, Jordi Burés

Organic Chemistry Group

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Abstract

Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.

Original language	English
Journal	The Journal of organic chemistry
Early online date	10 Feb 2021
DOIs	https://doi.org/10.1021/acs.joc.0c02998
Publication status	Published - 10 Feb 2021

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10.1021/acs.joc.0c02998

Bures lactolsAccepted author manuscript, 989 KB

https://pubs.acs.org/doi/10.1021/acs.joc.0c02998

JB EPSRC NIA Nov18
Bures, J. (PI)
1/10/18 → 30/09/20
Project: Research

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title = "Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols",

abstract = "Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.",

author = "Carla Alamillo-ferrer and Nielsen, {Christian D.-t.} and Andrea Salzano and Xavier Company{\'o} and {Di Sanza}, Riccardo and Spivey, {Alan C.} and Rzepa, {Henry S.} and Jordi Bur{\'e}s",

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doi = "10.1021/acs.joc.0c02998",

language = "English",

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T1 - Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols

AU - Alamillo-ferrer, Carla

AU - Nielsen, Christian D.-t.

AU - Salzano, Andrea

AU - Companyó, Xavier

AU - Di Sanza, Riccardo

AU - Spivey, Alan C.

AU - Rzepa, Henry S.

AU - Burés, Jordi

PY - 2021/2/10

Y1 - 2021/2/10

N2 - Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.

AB - Downstream intermediates are crucial for the reactivity and selectivity of aminocatalytic reactions. We present an analysis of the stereopreference in aminocatalytic downstream intermediates, which reveals an inconspicuous mechanism of chiral recognition between the catalyst and the rest of the molecule. We delineate a stereoelectronic model to rationalize the mode of chiral transmission. We also exploit it for the resolution of chiral lactols relevant in organic synthesis as well as in the flavor and fragrance industry.

U2 - 10.1021/acs.joc.0c02998

DO - 10.1021/acs.joc.0c02998

M3 - Article

SN - 0022-3263

JO - The Journal of organic chemistry

JF - The Journal of organic chemistry

ER -

Understanding the Diastereopreference of Intermediates in Aminocatalysis: Application to the Chiral Resolution of Lactols

Abstract

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Projects

JB EPSRC NIA Nov18

Cite this