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.
Highlights
Chiral compounds play an important role in areas such as asymmetric catalysis
After discovery of the axially chiral urazoles (Fig. 1b, compound D), we turned our attention to construct the chiral urazoles in an atroposelective approach via tyrosine click-like reaction
As part of our continued interest in the area of synthesis of axially chiral compounds[38] and asymmetric catalysis[39], we would like to exhibit the remote control of the axial chirality of arylurazoles by using a desymmetrization strategy via organocatalytic tyrosine click reaction of 4-aryl-1,2,4triazole-3,5-dione (ATAD)
Summary
Chiral compounds play an important role in areas such as asymmetric catalysis. After discovery of the axially chiral urazoles (Fig. 1b, compound D), we turned our attention to construct the chiral urazoles in an atroposelective approach via tyrosine click-like reaction In this scenario, three major challenges would be encountered: (1) the selection of suitable catalyst to interact with the substrates in high efficiency to inhibit the very strong background reaction; (2) the choice of an appropriate chiral catalyst prompt to efficiently induce remote axial enantiocontrol at the distant position via organocatalytic desymmetrization strategy[13,14,15,16,17,18,19]; (3) the use of mild reaction conditions to circumvent the axial rotation.
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