Anodic Cyclizations and Umpolung Reactions Involving Imines

Zach Medcalf; Essence G. Redd; Jaemyeong Oh; Chang Ji; Kevin D. Moeller

doi:10.1021/acs.orglett.3c01399

Anodic Cyclizations and Umpolung Reactions Involving Imines

Zach Medcalf, Essence G. Redd, Jaemyeong Oh, Chang Ji, Kevin D. Moeller

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Abstract

Recent discoveries that anodic cyclization reactions rely heavily on the success of a second electron oxidation downstream of the cyclization suggest that this second electron oxidation step can be used to channel a reaction down new synthetic pathways. Here we describe one such application that reverses the normal reactivity of an imine group and sets the stage for the asymmetric synthesis of cyclic amines by anodic cyclization.

Original language	English
Pages (from-to)	4135-4139
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.3c01399
State	Published - Jun 9 2023

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title = "Anodic Cyclizations and Umpolung Reactions Involving Imines",

abstract = "Recent discoveries that anodic cyclization reactions rely heavily on the success of a second electron oxidation downstream of the cyclization suggest that this second electron oxidation step can be used to channel a reaction down new synthetic pathways. Here we describe one such application that reverses the normal reactivity of an imine group and sets the stage for the asymmetric synthesis of cyclic amines by anodic cyclization.",

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AU - Medcalf, Zach

AU - Redd, Essence G.

AU - Oh, Jaemyeong

AU - Ji, Chang

AU - Moeller, Kevin D.

PY - 2023/6/9

Y1 - 2023/6/9

N2 - Recent discoveries that anodic cyclization reactions rely heavily on the success of a second electron oxidation downstream of the cyclization suggest that this second electron oxidation step can be used to channel a reaction down new synthetic pathways. Here we describe one such application that reverses the normal reactivity of an imine group and sets the stage for the asymmetric synthesis of cyclic amines by anodic cyclization.

AB - Recent discoveries that anodic cyclization reactions rely heavily on the success of a second electron oxidation downstream of the cyclization suggest that this second electron oxidation step can be used to channel a reaction down new synthetic pathways. Here we describe one such application that reverses the normal reactivity of an imine group and sets the stage for the asymmetric synthesis of cyclic amines by anodic cyclization.

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U2 - 10.1021/acs.orglett.3c01399

DO - 10.1021/acs.orglett.3c01399

M3 - Article

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SN - 1523-7060

VL - 25

SP - 4135

EP - 4139

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Anodic Cyclizations and Umpolung Reactions Involving Imines

Abstract

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