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Molecules 2018, 23(12), 3223; https://doi.org/10.3390/molecules23123223

DDQ-Promoted Mild and Efficient Metal-Free Oxidative α-Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines

1
College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University, 206 Worldcup-ro, Yeongtong-gu, Suwon 16499, Korea
2
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Gyeonggi-do, Pocheon 11160, Korea
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 26 November 2018 / Revised: 3 December 2018 / Accepted: 5 December 2018 / Published: 6 December 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

A mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)3SnCN. Employing readily removable N-acyl/sulfonyl groups as protecting groups rather than N-aryl ones enables a wide range of applications in natural product synthesis. The synthetic utility of the method was illustrated using a short and efficient formal total synthesis of (±)-calycotomine in three steps. View Full-Text
Keywords: tetrahydroisoquinoline; oxidation; C(sp3)-H activation; α-cyanation tetrahydroisoquinoline; oxidation; C(sp3)-H activation; α-cyanation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kim, H.P.; Yu, H.; Kim, H.; Kim, S.-H.; Lee, D. DDQ-Promoted Mild and Efficient Metal-Free Oxidative α-Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines. Molecules 2018, 23, 3223.

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