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Synthesis and X‐Ray Crystal Structure of an Optically Pure Tripodal C 3 ‐Symmetric Tritertiary Phosphine Bearing Chirality on Phosphorus
Author(s) -
Ward Thomas R.,
Venanzi Luigi M.,
Albinati Alberto,
Lianza Francesca,
Gerfin Tobias,
Gramlich Volker,
Tombo Gerardo M. Ramos
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740508
Subject(s) - chemistry , phosphine , borane , deprotonation , chirality (physics) , crystal structure , crystallography , axial chirality , carbanion , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , ion , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The preparation of the optically pure tritertiary phosphine (RRR)‐MeSi(CH2P(t‐Bu)Ph)3 (2) is reported. The route followed involves deprotonation of optically pure (R)‐P(BH3)Me(t‐Bu)PH (2) the reaction of the resulting carbanion with MeSiCl3, followed by removal with morpholine of the BH3‐protecting groups from the triertiary phosphine‐borane 3 . The latter's X‐ray crystal structure and that of [Rh(NBD)((RRR)‐ 1 ]TOf)( 4 ), are also rported. Furthermore, it is shown that the separation of the racemic phosphine‐borane 2 can be conveniently carried out using medium‐pressure liquid chromatgrapy with cellulose‐riacetate as a chiral stationary phase.