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Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

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.

SUBMITTER: Neel AJ

PROVIDER: S-EPMC4117382 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Neel Andrew J AJ Hehn Jörg P JP Tripet Pascal F PF Toste F Dean FD

Journal of the American Chemical Society 20130911 38

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 ster ...[more]

PMID: 24025163

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