Asymmetric Organocatalysis and Photoredox Catalysis for the α‐Functionalization of Tetrahydroisoquinolines. Issue 10 (14th March 2018)

• Record Type: Journal Article
• Authors: Hou, Hong; Zhu, Shaoqun; Atodiresei, Iuliana; Rueping, Magnus
• Is Part Of: European journal of organic chemistry. Issue 10(2018)
• Page Start: 1277
• Page End: 1280
• Publication Date: 2018-03-14
• Subjects: Cyclic ketones -- Tetrahydroisoquinolines -- Organocatalysis -- Photocatalysis -- Alkylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800117
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The asymmetric α‐alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible‐light photoredox catalyst and a chiral primary amine organocatalyst. The desired products were obtained in good yields, high enantioselectivity, and good to excellent diastereoselectivity. (PC: photoredox cycle, EN: enamine cycle). Abstract : A combined photoredox/organocatalytic system for the asymmetric α‐alkylation of tetrahydroisoquinolines (THIQs) has been developed. In this protocol, a chiral organocatalyst enables a high level of enantio‐ and diastereocontrol for the oxidative coupling reaction of THIQs with simple cyclic ketones.