Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams

Simon N. Smith; Cristina Trujillo; Stephen J. Connon

doi:10.1039/d2ob01040b

Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams

Simon N. Smith, Cristina Trujillo, Stephen J. Connon^*

^*Corresponding author for this work

Computational and Theoretical Chemistry

University of Dublin Trinity College

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

Abstract

An unprecedented organocatalytic process involving the asymmetric addition of azide to meso-anhydrides has been developed, promoted by novel sulfamide-substituted Cinchona alkaloid-based catalysts. Readily available glutaric anhydrides can be smoothly converted to enantioenriched hemi-acyl azides and from there to either γ-amino acids or γ-lactams.

Original language	English
Pages (from-to)	6384-6393
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	32
DOIs	https://doi.org/10.1039/d2ob01040b
Publication status	Published - 21 Jul 2022

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title = "Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams",

abstract = "An unprecedented organocatalytic process involving the asymmetric addition of azide to meso-anhydrides has been developed, promoted by novel sulfamide-substituted Cinchona alkaloid-based catalysts. Readily available glutaric anhydrides can be smoothly converted to enantioenriched hemi-acyl azides and from there to either γ-amino acids or γ-lactams.",

author = "Smith, {Simon N.} and Cristina Trujillo and Connon, {Stephen J.}",

note = "Funding Information: Financial support from the Irish Research Council (IRC GOIPG/2017/972) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

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doi = "10.1039/d2ob01040b",

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T1 - Catalytic, asymmetric azidations at carbonyls

T2 - achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams

AU - Smith, Simon N.

AU - Trujillo, Cristina

AU - Connon, Stephen J.

PY - 2022/7/21

Y1 - 2022/7/21

N2 - An unprecedented organocatalytic process involving the asymmetric addition of azide to meso-anhydrides has been developed, promoted by novel sulfamide-substituted Cinchona alkaloid-based catalysts. Readily available glutaric anhydrides can be smoothly converted to enantioenriched hemi-acyl azides and from there to either γ-amino acids or γ-lactams.

AB - An unprecedented organocatalytic process involving the asymmetric addition of azide to meso-anhydrides has been developed, promoted by novel sulfamide-substituted Cinchona alkaloid-based catalysts. Readily available glutaric anhydrides can be smoothly converted to enantioenriched hemi-acyl azides and from there to either γ-amino acids or γ-lactams.

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U2 - 10.1039/d2ob01040b

DO - 10.1039/d2ob01040b

M3 - Article

C2 - 35861618

AN - SCOPUS:85134960278

SN - 1477-0520

VL - 20

SP - 6384

EP - 6393

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 32

ER -

Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams

Abstract

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