Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction.

Abstract:

:Axially chiral compounds play an important role in areas such as asymmetric catalysis. The tyrosine click-like reaction is an efficient approach for synthesis of urazoles with potential applications in pharmaceutical and asymmetric catalysis. Here we discover a class of urazole with axial chirality by restricted rotation around an N-Ar bond. By using bifunctional organocatalyst, we successfully develop an organocatalytic asymmetric tyrosine click-like reaction in high yields with excellent enantioselectivity under mild reaction conditions. The excellent remote enantiocontrol of the strategy originates from the efficient discrimination of the two reactive sites in the triazoledione and transferring the stereochemical information of the catalyst into the axial chirality of urazoles at the remote position far from the reactive site.

journal_name

Nat Commun

journal_title

Nature communications

authors

Zhang JW,Xu JH,Cheng DJ,Shi C,Liu XY,Tan B

doi

10.1038/ncomms10677

subject

Has Abstract

pub_date

2016-02-11 00:00:00

pages

10677

issn

2041-1723

pii

ncomms10677

journal_volume

7

pub_type

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