Asymmetric Synthesis of Atropisomeric Amines via Transaminase-Catalyzed Dynamic Kinetic Resolution

J. M. Coto-Cid; P. Rodríguez-Salamanca; C. M. Heckmann; C. E. Paul; J. López-Serrano; Rosario Fernández; José M. Lassaletta; Valentín Hornillos; Gonzalo de Gonzalo

doi:10.1002/adsc.70254

Asymmetric Synthesis of Atropisomeric Amines via Transaminase-Catalyzed Dynamic Kinetic Resolution

J. M. Coto-Cid
, P. Rodríguez-Salamanca
, C. M. Heckmann
, C. E. Paul
, J. López-Serrano
, Rosario Fernández
, José M. Lassaletta^*
, Valentín Hornillos^*
, Gonzalo de Gonzalo^*

^*Corresponding author for this work

BT/Biocatalysis

Research output: Contribution to journal › Article › Scientific › peer-review

1 Citation (Scopus)

1 Downloads (Pure)

Abstract

Atropisomeric heterobiaryl primary amines are of significant interest in both organic and pharmaceutical chemistry. A series of transaminases have been employed to synthesize these valuable compounds with high yields (up to 98% conversion) and excellent enantioselectivities (up to ≥99% ee) via dynamic kinetic resolution of the corresponding heterobiaryl aldehydes. This process features a Lewis acid–base interaction strategy to facilitate labilization of the stereogenic axis.

Original language	English
Article number	e70254
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	368
Issue number	2
DOIs	https://doi.org/10.1002/adsc.70254
Publication status	Published - 2025

Keywords

atroposelective synthesis
dynamic kinetic resolutions
selective aminations
transaminases

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10.1002/adsc.70254

Adv Synth Catal - 2025 - Coto‐Cid - Asymmetric Synthesis of Atropisomeric Amines via Transaminase‐Catalyzed Dynamic KineticFinal published version, 781 KBLicence: CC BY

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title = "Asymmetric Synthesis of Atropisomeric Amines via Transaminase-Catalyzed Dynamic Kinetic Resolution",

abstract = "Atropisomeric heterobiaryl primary amines are of significant interest in both organic and pharmaceutical chemistry. A series of transaminases have been employed to synthesize these valuable compounds with high yields (up to 98\% conversion) and excellent enantioselectivities (up to ≥99\% ee) via dynamic kinetic resolution of the corresponding heterobiaryl aldehydes. This process features a Lewis acid–base interaction strategy to facilitate labilization of the stereogenic axis.",

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author = "Coto-Cid, \{J. M.\} and P. Rodr{\'i}guez-Salamanca and Heckmann, \{C. M.\} and Paul, \{C. E.\} and J. L{\'o}pez-Serrano and Rosario Fern{\'a}ndez and Lassaletta, \{Jos{\'e} M.\} and Valent{\'i}n Hornillos and Gonzalo, \{Gonzalo de\}",

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language = "English",

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journal = "Advanced Synthesis and Catalysis",

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T1 - Asymmetric Synthesis of Atropisomeric Amines via Transaminase-Catalyzed Dynamic Kinetic Resolution

AU - Coto-Cid, J. M.

AU - Rodríguez-Salamanca, P.

AU - Heckmann, C. M.

AU - Paul, C. E.

AU - López-Serrano, J.

AU - Fernández, Rosario

AU - Lassaletta, José M.

AU - Hornillos, Valentín

AU - Gonzalo, Gonzalo de

PY - 2025

Y1 - 2025

N2 - Atropisomeric heterobiaryl primary amines are of significant interest in both organic and pharmaceutical chemistry. A series of transaminases have been employed to synthesize these valuable compounds with high yields (up to 98% conversion) and excellent enantioselectivities (up to ≥99% ee) via dynamic kinetic resolution of the corresponding heterobiaryl aldehydes. This process features a Lewis acid–base interaction strategy to facilitate labilization of the stereogenic axis.

AB - Atropisomeric heterobiaryl primary amines are of significant interest in both organic and pharmaceutical chemistry. A series of transaminases have been employed to synthesize these valuable compounds with high yields (up to 98% conversion) and excellent enantioselectivities (up to ≥99% ee) via dynamic kinetic resolution of the corresponding heterobiaryl aldehydes. This process features a Lewis acid–base interaction strategy to facilitate labilization of the stereogenic axis.

KW - atroposelective synthesis

KW - dynamic kinetic resolutions

KW - selective aminations

KW - transaminases

UR - https://www.scopus.com/pages/publications/105022904595

U2 - 10.1002/adsc.70254

DO - 10.1002/adsc.70254

M3 - Article

AN - SCOPUS:105022904595

SN - 1615-4150

VL - 368

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 2

M1 - e70254

ER -

Asymmetric Synthesis of Atropisomeric Amines via Transaminase-Catalyzed Dynamic Kinetic Resolution

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