P-stereogenic wide bite angle diphosphine ligands

Christine F. Czauderna; Alexandra M. Z. Slawin; David B. Cordes; Jarl Ivar van der Vlugt; Paul C.J. Kamer

doi:10.1016/j.tet.2018.10.070

P-stereogenic wide bite angle diphosphine ligands

Christine F. Czauderna, Alexandra M. Z. Slawin, David B. Cordes, Jarl Ivar van der Vlugt, Paul C.J. Kamer

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

Abstract

Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed, leading to compounds (S,S)-2,2′-bis(methylphenylphosphino)diphenyl ether (L1) and (S,S)-2,2′-bis(ferrocenylphenylphosphino)diphenyl ether (L2) in very good diastereomeric ratios. Both protocols involve diphenyl ether as backbone and (2R_P,4S_C,5R_C)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane (R_P)-5 as initial auxiliary to induce chirality at phosphorus. The absolute configuration of intermediates (S,S)-9-(BH₃)₂ and (R,R)-10-(BH₃)₂ as well as the ligands (S,S)-L1-BH3 and (S,S)-L2 was determined by X-ray crystallographic analysis.

Original language	English
Pages (from-to)	47-56
Journal	Tetrahedron
Volume	75
Issue number	1
Early online date	14 Nov 2018
DOIs	https://doi.org/10.1016/j.tet.2018.10.070
Publication status	Published - 3 Jan 2019

Keywords

P-stereogenic ligand
Wide bite angle ligand
Ephedrine
Phosphinite borane
Oxazaphospholidine

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10.1016/j.tet.2018.10.070

Czauderna_2018_Tetrahedron_P-stereogenic_AAM
Copyright © 2018 Elsevier Ltd. All rights reserved. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2018.10.070
Accepted author manuscript, 722 KBLicence: CC BY-NC-ND

P-stereogenic wide bite angle diphosphine ligands (dataset)
Czauderna, C. F. (Creator), Slawin, A. M. Z. (Creator), Cordes, D. B. (Creator), van der Vlugt, J. I. (Creator) & Kamer, P. C. J. (Creator), Cambridge Crystallographic Data Centre, 26 Nov 2018
https://dx.doi.org/10.5517/ccdc.csd.cc1mx90v and 3 more links, https://dx.doi.org/10.5517/ccdc.csd.cc1mx91w, https://dx.doi.org/10.5517/ccdc.csd.cc1mx92x, https://dx.doi.org/10.5517/ccdc.csd.cc1mx93y (show fewer)
Dataset

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@article{340224fa6d48451d839e01e9c3743eca,

title = "P-stereogenic wide bite angle diphosphine ligands",

abstract = "Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed, leading to compounds (S,S)-2,2′-bis(methylphenylphosphino)diphenyl ether (L1) and (S,S)-2,2′-bis(ferrocenylphenylphosphino)diphenyl ether (L2) in very good diastereomeric ratios. Both protocols involve diphenyl ether as backbone and (2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane (RP)-5 as initial auxiliary to induce chirality at phosphorus. The absolute configuration of intermediates (S,S)-9-(BH3)2 and (R,R)-10-(BH3)2 as well as the ligands (S,S)-L1-BH3 and (S,S)-L2 was determined by X-ray crystallographic analysis.",

keywords = "P-stereogenic ligand, Wide bite angle ligand, Ephedrine, Phosphinite borane, Oxazaphospholidine",

author = "Czauderna, {Christine F.} and Slawin, {Alexandra M. Z.} and Cordes, {David B.} and {van der Vlugt}, {Jarl Ivar} and Kamer, {Paul C.J.}",

note = "This work was supported by an EASTCHEM fellowship. We would like to acknowledge the European Union for additional funding through a Marie Curie Excellence Grant MEXT-2004-014320 and COST action CM0802 PhoSciNet.",

year = "2019",

month = jan,

day = "3",

doi = "10.1016/j.tet.2018.10.070",

language = "English",

volume = "75",

pages = "47--56",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - P-stereogenic wide bite angle diphosphine ligands

AU - Czauderna, Christine F.

AU - Slawin, Alexandra M. Z.

AU - Cordes, David B.

AU - van der Vlugt, Jarl Ivar

AU - Kamer, Paul C.J.

N1 - This work was supported by an EASTCHEM fellowship. We would like to acknowledge the European Union for additional funding through a Marie Curie Excellence Grant MEXT-2004-014320 and COST action CM0802 PhoSciNet.

PY - 2019/1/3

Y1 - 2019/1/3

N2 - Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed, leading to compounds (S,S)-2,2′-bis(methylphenylphosphino)diphenyl ether (L1) and (S,S)-2,2′-bis(ferrocenylphenylphosphino)diphenyl ether (L2) in very good diastereomeric ratios. Both protocols involve diphenyl ether as backbone and (2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane (RP)-5 as initial auxiliary to induce chirality at phosphorus. The absolute configuration of intermediates (S,S)-9-(BH3)2 and (R,R)-10-(BH3)2 as well as the ligands (S,S)-L1-BH3 and (S,S)-L2 was determined by X-ray crystallographic analysis.

AB - Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed, leading to compounds (S,S)-2,2′-bis(methylphenylphosphino)diphenyl ether (L1) and (S,S)-2,2′-bis(ferrocenylphenylphosphino)diphenyl ether (L2) in very good diastereomeric ratios. Both protocols involve diphenyl ether as backbone and (2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane (RP)-5 as initial auxiliary to induce chirality at phosphorus. The absolute configuration of intermediates (S,S)-9-(BH3)2 and (R,R)-10-(BH3)2 as well as the ligands (S,S)-L1-BH3 and (S,S)-L2 was determined by X-ray crystallographic analysis.

KW - P-stereogenic ligand

KW - Wide bite angle ligand

KW - Ephedrine

KW - Phosphinite borane

KW - Oxazaphospholidine

U2 - 10.1016/j.tet.2018.10.070

DO - 10.1016/j.tet.2018.10.070

M3 - Article

SN - 0040-4020

VL - 75

SP - 47

EP - 56

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

P-stereogenic wide bite angle diphosphine ligands

Abstract

Keywords

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Datasets

P-stereogenic wide bite angle diphosphine ligands (dataset)

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