Catalytic asymmetric synthesis of {alpha}-amino phosphonates using lanthanoid-potassium-BINOL complexes
- Univ. of Tokyo (Japan); and others
{alpha}-Amino phosphonic acids 3 are interesting compounds in the design of enzyme inhibitors. The concept of mimicking tetrahedral transition states of enzyme-medicated peptide bond hydrolysis previously led to the successful design and synthesis of phosphonamide-containing peptides as a promising new class of proteinase inhibitors. It is not surprising that the absolute configuration of the {alpha}-carbon strongly influences the biological properties of 3. Several methods for the synthesis of optically active {alpha}-aminophosphonic acids have been published. The authors report here the first example of a catalytic asymmetric hydrophosphonylation to imines using lanthanoid-potassium-BINOL heterobimetallic complexes (LnPB, Ln = lanthanoid metal), which gives optically active {alpha}-amino phosphonates in modest to high enantiometric excess. 17 refs., 1 tab.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 274004
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 21 Vol. 60; ISSN 0022-3263; ISSN JOCEAH
- Country of Publication:
- United States
- Language:
- English
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