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Synthese optisch aktiver Nickel‐Komplexe mit porphinoidem Ligandsystem
Author(s) -
Vogel Ulrich,
Meier Kurt,
Löliger Jürg,
Scheffold Rolf
Publication year - 1981
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.19810640416
Subject(s) - chemistry , adduct , nickel , diastereomer , iodide , methyl iodide , medicinal chemistry , enantiomer , optically active , stereochemistry , organic chemistry
Synthesis of Optically Active Porphine‐type Nickel Complexes Both enantiomers of [1‐methyl‐8 H‐HDP]nickel‐perchlorate For nomenclature see footnote 5 in this paper. ( 2a and 2b , respectively) have been synthesized by the following reaction sequence: (a) base induced addition of (−)‐( R )‐2‐octanol to 1 , (b) separation of the two diastereomeric monoadducts 4a and 4b , (c) reaction with methyl magnesium iodide containing an excess of methyl iodide, (d) acid induced elimination of 2‐octanol from the diadducts 6a and 6b . By a similar procedure both enantiomers of [1‐butyl‐8 H‐HDP] nickel‐perchlorate ( 3a and 3b , respectively) have been prepared. The reaction of 3a with butyl lithium yields in a kinetically controlled addition predominantly the optically active cis ‐1, 11‐dibutyl adduct 8 and in minor quantity the meso ‐ cis ‐1, 11‐dibutyl adduct 9 .