P-stereogenic wide bite angle diphosphine ligands
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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.
Czauderna , C F , Slawin , A M Z , Cordes , D B , van der Vlugt , J I & Kamer , P C J 2019 , ' P-stereogenic wide bite angle diphosphine ligands ' , Tetrahedron , vol. 75 , no. 1 , pp. 47-56 . https://doi.org/10.1016/j.tet.2018.10.070
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
DescriptionThis 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.
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