Work

Asymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids

Year: 2013

Type: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja407410b

Authors: Andrew J. Neel, Jörg P. Hehn, Pascal F. Tripet, F. Dean Toste

Institution: University of California, Berkeley

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, Deutsche Akademie der Naturforscher Leopoldina - Nationale Akademie der Wissenschaften, National Institute of General Medical Sciences

Award: Enantioselective Synthesis by Chiral Anion Phase Transfer Catalysis