Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction

Rifhat Bibi; Ismat Ullah Khan; Abbas Hassan

doi:10.1016/j.tetlet.2022.154204

Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction

Rifhat Bibi
, Ismat Ullah Khan
, Abbas Hassan

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

3 Citations (Scopus)

Abstract

A structure selectivity relationship was established by systematically increasing the steric of the ligands from phenyl substituent to mesityl on the pyridine ring of Pyox and isopropyl to tert-butyl group on the oxazoline ring. The ligand ⁶MesPyox^sBu bearing a sterically demanding mesityl group at position 6 of the pyridine ring showed optimum catalytic activity for Heck-Matsuda desymmetrization reaction of non-activated cyclopentene using Pd(tfa)₂ as the catalyst. A wide range of arenediazonium salts bearing electronically distinct substituents was evaluated in Heck-Matsuda coupling, which resulted in good to excellent isolated yields (67–92 %), excellent enantio- and diastereoselectivity (up to 96 % ee, >20:1 dr).

Original language	English
Article number	154204
Journal	Tetrahedron Letters
Volume	111
DOIs	https://doi.org/10.1016/j.tetlet.2022.154204
Publication status	Published - Nov 23 2022
Externally published	Yes

Keywords

Enantioselective Heck-Matsuda reaction
Ligand development
Pyridine-oxazoline ligand
Steric evaluation
Structure selectivity relationship

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2022.154204

Cite this

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title = "Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction",

abstract = "A structure selectivity relationship was established by systematically increasing the steric of the ligands from phenyl substituent to mesityl on the pyridine ring of Pyox and isopropyl to tert-butyl group on the oxazoline ring. The ligand 6MesPyoxsBu bearing a sterically demanding mesityl group at position 6 of the pyridine ring showed optimum catalytic activity for Heck-Matsuda desymmetrization reaction of non-activated cyclopentene using Pd(tfa)2 as the catalyst. A wide range of arenediazonium salts bearing electronically distinct substituents was evaluated in Heck-Matsuda coupling, which resulted in good to excellent isolated yields (67–92 \%), excellent enantio- and diastereoselectivity (up to 96 \% ee, >20:1 dr).",

keywords = "Enantioselective Heck-Matsuda reaction, Ligand development, Pyridine-oxazoline ligand, Steric evaluation, Structure selectivity relationship",

author = "Rifhat Bibi and Khan, \{Ismat Ullah\} and Abbas Hassan",

note = "Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = nov,

day = "23",

doi = "10.1016/j.tetlet.2022.154204",

language = "English",

volume = "111",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction

AU - Bibi, Rifhat

AU - Khan, Ismat Ullah

AU - Hassan, Abbas

PY - 2022/11/23

Y1 - 2022/11/23

N2 - A structure selectivity relationship was established by systematically increasing the steric of the ligands from phenyl substituent to mesityl on the pyridine ring of Pyox and isopropyl to tert-butyl group on the oxazoline ring. The ligand 6MesPyoxsBu bearing a sterically demanding mesityl group at position 6 of the pyridine ring showed optimum catalytic activity for Heck-Matsuda desymmetrization reaction of non-activated cyclopentene using Pd(tfa)2 as the catalyst. A wide range of arenediazonium salts bearing electronically distinct substituents was evaluated in Heck-Matsuda coupling, which resulted in good to excellent isolated yields (67–92 %), excellent enantio- and diastereoselectivity (up to 96 % ee, >20:1 dr).

AB - A structure selectivity relationship was established by systematically increasing the steric of the ligands from phenyl substituent to mesityl on the pyridine ring of Pyox and isopropyl to tert-butyl group on the oxazoline ring. The ligand 6MesPyoxsBu bearing a sterically demanding mesityl group at position 6 of the pyridine ring showed optimum catalytic activity for Heck-Matsuda desymmetrization reaction of non-activated cyclopentene using Pd(tfa)2 as the catalyst. A wide range of arenediazonium salts bearing electronically distinct substituents was evaluated in Heck-Matsuda coupling, which resulted in good to excellent isolated yields (67–92 %), excellent enantio- and diastereoselectivity (up to 96 % ee, >20:1 dr).

KW - Enantioselective Heck-Matsuda reaction

KW - Ligand development

KW - Pyridine-oxazoline ligand

KW - Steric evaluation

KW - Structure selectivity relationship

UR - https://www.scopus.com/pages/publications/85140641463

UR - https://www.scopus.com/pages/publications/85140641463#tab=citedBy

U2 - 10.1016/j.tetlet.2022.154204

DO - 10.1016/j.tetlet.2022.154204

M3 - Article

AN - SCOPUS:85140641463

SN - 0040-4039

VL - 111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154204

ER -

Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction

Abstract

Keywords

ASJC Scopus subject areas

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