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New Rare-Earth BINOLate Compounds

Air and Moisture Stable REMB/Shibasaki Precatalysts for Asymmetric Synthesis

Shibasaki catalysts have been applied successfully to asymmetric synthesis challenges in the fine chemical and pharmaceutical industries for the past 25 years.  The catalysts are particularly interesting due to their tunability and success in providing high yield and high enantioselective transformation in, but not limited to, Direct Aldol, Hydrophosphonylation, and Aza-Michael addition reactions.  The challenges that prevent Shibasaki catalysts from greater adoption in the industry have been the strict air free and anhydrous conditions required to keep the sensitive catalysts active.   

Professor Walsh’s and Professor Schelter’s labs at the University of Pennsylvania have solved the problems of handling REMB catalysts by creating a robust precatalyst that self-assembles REMB/Shibasaki frameworks in open air and wet solvent conditions.  The new precatalysts allow trouble-free handling and tunability through varying the alkali salts and amines to assemble the active catalysts.  These improvements greatly enhance the ability to screen and optimize REMB catalysts for specific enantioselective reactions at the bench and by high throughput screening.

Framework

The above image is courtesy of the University of Pennsylvania

 

57-1250  59-1000

70-0130  39-5850

 

 

Reference:

  1.        J. Am. Chem. Soc., 2014, 136, 8034.

 

 

Products related to this blog:

57-1250: Tris[N,N,N,N-tetramethylguanidinium][tris(1S)-(1,1-binaphalene)-2,2-diolato]lanthanate La-HTMG-B [1611526-71-6]

59-1000: Tris[N,N,N,N-tetramethylguanidinium][tris(1S)-(1,1-binaphalene)-2,2-diolato]praseodymate Pr-HTMG-B

70-0130: Tris[N,N,N,N-tetramethylguanidinium][tris(1S)-(1,1-binaphalene)-2,2-diolato]ytterbate Yb-HTMG-B [1611526-75-0]

39-5850: Tris[N,N,N,N-tetramethylguanidinium][tris(1S)-(1,1-binaphalene)-2,2-diolato]yttrate Y-HTMG-B [1611526-73-8] 

 

Related literature:

Rare-Earth BINOLate Compounds

 

 

 

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