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From Heteroaromatic acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis

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JournalChemistry : A European Journal (Weinheim an der Bergstrasse, Germany)
DateAccepted/In press - 22 Feb 2016
DateE-pub ahead of print - 25 Feb 2016
DatePublished (current) - 2016
Issue number19
Volume22
Number of pages5
Pages (from-to)6496-6500
Early online date25/02/16
Original languageEnglish

Abstract

Heteroaromatic carboxylic acids have been directly coupled with imines using T3P and NEt(i-Pr)2 to form azaspirocycles via intermediate N-acyliminium ions. Spirocyclic indolenines (3H-indoles), azaindolenines, 2H-pyrroles and 3H-pyrroles were all accessed using this metal-free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under-represented in existing drugs and high throughput screening libraries.

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© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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