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.
Citation
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
Publication
Tetrahedron
Status
Peer reviewed
ISSN
0040-4020Type
Journal article
Description
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.Collections
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