Synthesis of 3-aminoindenes and cis-1-aminoindanes by Zn(OTf)2-catalyzed cyclization of o-alkynylbenzaldehydes with tertiary alkyl primary amines
Literature Information
Tuanli Yao, Rui Zhu, Tao Liu
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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