Synthesis of 3-aminoindenes and cis-1-aminoindanes by Zn(OTf)2-catalyzed cyclization of o-alkynylbenzaldehydes with tertiary alkyl primary amines

Literature Information

Publication Date 2023-11-06
DOI 10.1039/D3CC04180H
Impact Factor 6.222
Authors

Tuanli Yao, Rui Zhu, Tao Liu


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Abstract

Using Zn(OTf)2 as catalyst, a highly regio- and chemo-selective cyclocarboamination of o-alkynylbenzaldehydes with tertiary alkyl primary amines was realized to access 3-aminoindenes with different substitution patterns from previously reported methods. The full reduction of the iminoindenone intermediates affords cis-1-amino-2-arylindanes with excellent diastereoselectivity. Mechanistically, the reaction involves the rearrangement of 1-amino-3-arylidene-isoindolines and isomerization of 1-aminoindenes to 3-aminoindenes.

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Chemical Communications

Chemical Communications
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