Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis

Christian Borch Jacobsen; Daniel Steen Nielsen; Morten Meldal; Frederik Diness

doi:10.1021/acs.joc.9b00732

Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis

Christian Borch Jacobsen, Daniel Steen Nielsen, Morten Meldal^*, Frederik Diness

^*Corresponding author for this work

Department of Chemistry

1 Citation (Scopus)

Abstract

Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hetero Diels-Alder adducts. A rational for the observed enantioselectivity and conversion rate supported by computational calculations is provided.

Original language	English
Journal	Journal of Organic Chemistry
Volume	84
Issue number	11
Pages (from-to)	6940-6945
Number of pages	6
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.9b00732
Publication status	Published - 7 Jun 2019

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title = "Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis",

abstract = "Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hetero Diels-Alder adducts. A rational for the observed enantioselectivity and conversion rate supported by computational calculations is provided.",

author = "Jacobsen, {Christian Borch} and Nielsen, {Daniel Steen} and Morten Meldal and Frederik Diness",

year = "2019",

month = jun,

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language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis

AU - Jacobsen, Christian Borch

AU - Nielsen, Daniel Steen

AU - Meldal, Morten

AU - Diness, Frederik

PY - 2019/6/7

Y1 - 2019/6/7

N2 - Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hetero Diels-Alder adducts. A rational for the observed enantioselectivity and conversion rate supported by computational calculations is provided.

AB - Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hetero Diels-Alder adducts. A rational for the observed enantioselectivity and conversion rate supported by computational calculations is provided.

U2 - 10.1021/acs.joc.9b00732

DO - 10.1021/acs.joc.9b00732

M3 - Journal article

C2 - 31033291

AN - SCOPUS:85066611116

SN - 0022-3263

VL - 84

SP - 6940

EP - 6945

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis

Abstract

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