AI Article Synopsis
- The report outlines a new method for creating enantioselective C-N bonds to produce cyclic aminals from 1,2,3,4-tetrahydroisoquinoline using chiral phosphate anions as catalysts.
- Key to this method was the development of a library of phosphoric acids derived from 3,3'-triazolyl BINOL, designed to enhance hydrogen-bonding interactions with the substrate.
- This research aims to provide an alternative approach to improving enantioselectivity by focusing on molecular interactions rather than just increasing the steric bulk of the catalyst.
Article Abstract
This report describes the development of an enantioselective C-N bond-forming reaction to produce 1,2,3,4-tetrahydroisoquinoline-derived cyclic aminals catalyzed by chiral phosphate anions. Central to the success of this goal was the design of a library of 3,3'-triazolyl BINOL-derived phosphoric acids capable of forming attractive hydrogen-bonding interactions with the peptide-like substrate. We envision this work will offer an alternative to the conventional strategy of increasing catalyst steric bulk to improve enantioselectivity with BINOL-derived phosphoric acids.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4117382 | PMC |
| http://dx.doi.org/10.1021/ja407410b | DOI Listing |
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