Optically active 1,1'-biphenanthryl-2,2'-diol, process for prepa

Details Optically active 1,1'-biphenanthryl-2,2'-diol, process for prepa Optically active 1,1'-biphenanthryl-2,2'-diol, process for prepa

1997-03-07

1998-12-15

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 3542

Patent

active

058499610

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.

REFERENCES:
The Journal of the American Chemical Society, Nov. 3, 1993, vol. 115, No. 22, pp. 10372/10373, Hiroaki Sasai et al, "Catalytic Asymmetric Nitroaldol Reaction Using Optically Active Rare Earth BINOL Complexes: Investigation of the Catalyst.".
The Journal of the Organic Chemistry, Nov. 18, 1994, vol. 59, No. 23, Dongwei Cai et al, "Synthesis of Chiral 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl )BINAP) via a Novel Nickel-Catalyzed Phosphine Insertion.".
Yamamura, K. et al, `Chiral Liquid Crystal Mesogens. Synthesis and Determination of Absolute Configuration of Mesogens With 4,4'-Biphenanthryl Cores` Synlett. 1989, 1, pp. 18-19, abstract only.

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