Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

Matteo Faltracco; Silvia Cotogno; Christophe M.L. Vande Velde; Eelco Ruijter

doi:10.1021/acs.joc.9b01994

Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

Matteo Faltracco, Silvia Cotogno, Christophe M.L. Vande Velde, Eelco Ruijter

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

Original language	English
Pages (from-to)	12058-12070
Number of pages	13
Journal	The Journal of organic chemistry
Volume	84
Issue number	18
Early online date	26 Aug 2019
DOIs	https://doi.org/10.1021/acs.joc.9b01994
Publication status	Published - 20 Sep 2019

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AU - Ruijter, Eelco

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Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

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CCDC 1902629: Experimental Crystal Structure Determination

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Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

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CCDC 1902629: Experimental Crystal Structure Determination

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