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Diastereoselective Synthesis of Functionalized Indoline N , O ‐Aminals: Unexpected Water‐Involved Cascade Reaction of 3 H ‐Indoles and Oxazol‐5‐(4 H )ones
Author(s) -
Cheng DaoJuan,
Li RuiQi,
Zhang XingShuai,
Zhao Lin,
Wang Tao,
Shao YouDong
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901774
Subject(s) - chemistry , indoline , moiety , domino , cascade reaction , catalysis , combinatorial chemistry , cascade , stereochemistry , organic chemistry , chromatography
Herein, we describe an unexpected TsOH · H 2 O‐mediated domino three‐component reaction of 3 H ‐indoles, oxazol‐5‐(4 H )ones, and water, allowing rapid access to a new family of structurally unique indoline N , O ‐aminals bearing a valuable α‐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.