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A Novel Approach to Ferrocenes with Planar Chirality
Author(s) -
Ganter Christian,
Wagner Trixie
Publication year - 1995
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19951281204
Subject(s) - chemistry , ferrocene , metalation , moiety , acetic anhydride , diastereomer , chirality (physics) , denticity , ligand (biochemistry) , stereochemistry , medicinal chemistry , chelation , planar chirality , metallocene , quenching (fluorescence) , crystal structure , crystallography , enantioselective synthesis , catalysis , organic chemistry , receptor , chiral symmetry breaking , quark , polymer , biochemistry , quantum mechanics , nambu–jona lasinio model , electrochemistry , polymerization , physics , electrode , fluorescence
The 2‐metalation of enantiomerically pure ( S )‐(2‐methoxy‐methylpyrrolidin‐1‐yl)ferrocene FcSMP ( 1 ) with BuLi proceeds with high diastereoselectivity (up to 98% de) to yield the Ph 2 P‐substituted ferrocene ( S,S p )‐ 2a after quenching with Ph 2 PCl. The SMP moiety was removed by heating of 2a at reflux in acetic anhydride to give planar chiral ( S p )‐2‐diphenylphosphanylferrocenylmethyl acetate ( 5 ). The diastereoisomer ( S,R p )‐ 2b was synthesized from 1 by intermediately blocking the primary metalation site with a Me 3 Si group which can be removed afterwards by treatment with KO t Bu in DMSO. Compound 2a was treated with [(C 3 H 5 )PdCl] 2 to give the complex [(C 3 H 5 )Pd· 2a ]PF 6 ( 7 ·PF 6 ). The structure of 7 ·PF 6 was determined by a single‐crystal X‐ray diffraction study and showed 2a to act as a bidentate P,N ‐chelate ligand.
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