New P-chirogenic tert.-butyl-xantphos ligands and their application in asymmetric hydrogenation and alkylation

Jens Holz; Gudrun Wenzel; Anke Spannenberg; Mark Gandelman; Armin Börner

doi:10.1016/j.tet.2020.131142

New P-chirogenic tert.-butyl-xantphos ligands and their application in asymmetric hydrogenation and alkylation

Jens Holz
, Gudrun Wenzel
, Anke Spannenberg
, Mark Gandelman
, Armin Börner

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

8 Scopus citations

Abstract

The synthesis of a broad library of new P-chirogenic Xantphos ligands is reported. A special feature is 2,7-di-tert.-butyl substituents in the backbone which requires the modification of the original synthetic approach. In comparison to related ligands reported formerly the substitution has a considerable influence on the results (yield and % e.e.) of metal catalyzed reactions, e.g. asymmetric rhodium catalyzed hydrogenation of isophorone and the palladium catalyzed alkylation, respectively.

Original language	English
Article number	131142
Journal	Tetrahedron
Volume	76
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2020.131142
State	Published - 24 Apr 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Ltd

Funding

Dr. Ch. Fischer, Mrs. S. Buchholz, and Mrs. S. Schareina are acknowledged for careful analysis of reaction products. We thank for financial support by the German-Israeli Foundation for Scientific Research and Development (GIF, Research Agreement project I-1369-302.5/2016 ).

Funders	Funder number
German-Israeli Foundation for Scientific Research and Development	I-1369-302.5/2016

Keywords

Asymmetric allylic alkylation
Asymmetric hydrogenation
P-Chirogenic phosphines
Palladium
Rhodium
Xantphos

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10.1016/j.tet.2020.131142

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title = "New P-chirogenic tert.-butyl-xantphos ligands and their application in asymmetric hydrogenation and alkylation",

abstract = "The synthesis of a broad library of new P-chirogenic Xantphos ligands is reported. A special feature is 2,7-di-tert.-butyl substituents in the backbone which requires the modification of the original synthetic approach. In comparison to related ligands reported formerly the substitution has a considerable influence on the results (yield and \% e.e.) of metal catalyzed reactions, e.g. asymmetric rhodium catalyzed hydrogenation of isophorone and the palladium catalyzed alkylation, respectively.",

keywords = "Asymmetric allylic alkylation, Asymmetric hydrogenation, P-Chirogenic phosphines, Palladium, Rhodium, Xantphos",

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AU - Holz, Jens

AU - Wenzel, Gudrun

AU - Spannenberg, Anke

AU - Gandelman, Mark

AU - Börner, Armin

PY - 2020/4/24

Y1 - 2020/4/24

N2 - The synthesis of a broad library of new P-chirogenic Xantphos ligands is reported. A special feature is 2,7-di-tert.-butyl substituents in the backbone which requires the modification of the original synthetic approach. In comparison to related ligands reported formerly the substitution has a considerable influence on the results (yield and % e.e.) of metal catalyzed reactions, e.g. asymmetric rhodium catalyzed hydrogenation of isophorone and the palladium catalyzed alkylation, respectively.

AB - The synthesis of a broad library of new P-chirogenic Xantphos ligands is reported. A special feature is 2,7-di-tert.-butyl substituents in the backbone which requires the modification of the original synthetic approach. In comparison to related ligands reported formerly the substitution has a considerable influence on the results (yield and % e.e.) of metal catalyzed reactions, e.g. asymmetric rhodium catalyzed hydrogenation of isophorone and the palladium catalyzed alkylation, respectively.

KW - Asymmetric allylic alkylation

KW - Asymmetric hydrogenation

KW - P-Chirogenic phosphines

KW - Palladium

KW - Rhodium

KW - Xantphos

UR - https://www.scopus.com/pages/publications/85082011075

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AN - SCOPUS:85082011075

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 17

M1 - 131142

ER -

New P-chirogenic tert.-butyl-xantphos ligands and their application in asymmetric hydrogenation and alkylation

Abstract

Bibliographical note

Funding

Keywords

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