Optically active 1,1'-biphenanthryl-2,2'-diol, process for preparing the same, and resolving reagent comprising the same
AssigneeTakasago International Corporation
InventorsSotaro Miyano, Kenta Sakurai, Nobuyuki Koike, Tetsutaro Hattori
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Abstract
The novel optically active 1,1'-biphenanthryl-2,2'-diol is disclosed, which is obtained by preparing N((S)-1-phenylethyl)-1,1'-biphenanthryl-2,2'-diylthiophosphorylamide by using optically active phenylethylamine, recrystallizing the compound into an optically active compound, followed by reduction with a reducing agent. The diol compound according to the present invention is useful as a resolving reagent, a starting material of an optically active phosphine compound or a ligand in asymmetric synthesis, forming a complex with a transition metal or a rare earth element to provide a useful catalyst.
Claims5
1,1'-Biphenanthryl-2,2'-diol represented by formula (I):
- ##STR6##
Optically active 1,1'-biphenanthryl-2,2'-diol represented by formula (II):
- ##STR7##
A process for preparing optically active 1,1'-biphenanthryl-2,2'-diol comprising preparing a complex from a copper salt and an amine, reacting 2-phenanthrol in the presence of the complex to form (.+-.)-1,1'-biphenanthryl-2,2'-diol, reacting the (.+-.)-1,1'-biphenanthryl-2,2'-diol with thiophosphoryl chloride and optically active phenylethylamine in the presence of pyridine to form N-(1-phenylethyl)-1,1'-biphenanthryl-2,2'-diylthiophosphoramide, optically resolving the N-(1-phenylethyl)-1,1'-biphenanthryl-2,2'-diylthiophosphoramide by recrystallization, and hydrogenolyzing the resulting optically active compound.
In a method for resolving a compound using a resolving reagent, the improvement wherein the resolving reagent comprises optically active 1,1'-biphenanthryl-2,2'-diol represented by formula (II):
- ##STR8##
Dependencies are inferred from the claim text.