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Diastereoselective Synthesis of Functionalized Indoline N,O-Aminals: Unexpected Water-Involved Cascade Reaction of 3H-Indoles and Oxazol-5-(4H)ones
Herein, we describe an unexpected TsOH center dot H2O-mediated domino three-component reaction of 3H-indoles, oxazol-5-(4H)ones, and water, allowing rapid access to a new family of structurally unique indoline N,O-aminals bearing a valuable alpha-acylaminoamide moiety in high yields and excellent diastereoselectivities. The scaled-up experiment and various transformations of the products further demonstrate the utility of this chemistry. Moreover, a preliminary study on the catalytic asymmetric version of this novel 1,2-difunctionalization reaction is performed.
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