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Open AccessArticle

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

by Hong Pyo Kim 1,†, Heesun Yu 1,†, Hyoungsu Kim 1, Seok-Ho Kim 2,* and Dongjoo Lee 1,*
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
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Roman Dembinski
Molecules 2018, 23(12), 3223; https://doi.org/10.3390/molecules23123223
Received: 26 November 2018 / Revised: 3 December 2018 / Accepted: 5 December 2018 / Published: 6 December 2018
(This article belongs to the Section Organic Chemistry)
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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MDPI and ACS Style

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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