Quinone-catalyzed Oxidative Deformylation: Synthesis of Imines from Amino Alcohols

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2018 Mar 23

PMID 29564017

Authors

Xinyun Liu

Johnny H Phan

Benjamin J Haugeberg

Shrikant S Londhe

Michael D Clift

Affiliations

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Abstract

A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage.

References

Jiang G, Chen J, Huang J, Che C . Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions. Org Lett. 2009; 11(20):4568-71. DOI: 10.1021/ol9018166. View

Zhu S, Rueping M . Merging visible-light photoredox and Lewis acid catalysis for the functionalization and arylation of glycine derivatives and peptides. Chem Commun (Camb). 2012; 48(98):11960-2. DOI: 10.1039/c2cc36995h. View

Nancy , Ghosh S, Singh N, Kaur Nanda G, Venugopalan P, Bharatam P . Origin of 1,3-induction in the addition of alkyl lithium to imines bearing an N-stereogenic center. Chem Commun (Camb). 2003; (12):1420-1. DOI: 10.1039/b300478c. View

Park J, Ko K, Kim E, Park N, Ko J, Ryu D . Photocatalysis by phenothiazine dyes: visible-light-driven oxidative coupling of primary amines at ambient temperature. Org Lett. 2012; 14(21):5502-5. DOI: 10.1021/ol302584y. View

Weiner B, Szymanski W, Janssen D, Minnaard A, Feringa B . Recent advances in the catalytic asymmetric synthesis of beta-amino acids. Chem Soc Rev. 2010; 39(5):1656-91. DOI: 10.1039/b919599h. View

Zhu B, Angelici R . Non-nanogold catalyzed aerobic oxidation of secondary amines to imines. Chem Commun (Camb). 2007; (21):2157-9. DOI: 10.1039/b700555e. View

Rueping M, Zhu S, Koenigs R . Photoredox catalyzed C-P bond forming reactions-visible light mediated oxidative phosphonylations of amines. Chem Commun (Camb). 2011; 47(30):8679-81. DOI: 10.1039/c1cc12907d. View

Wang J, Lu S, Cao X, Gu H . Common metal of copper(0) as an efficient catalyst for preparation of nitriles and imines by controlling additives. Chem Commun (Camb). 2014; 50(42):5637-40. DOI: 10.1039/c4cc01389a. View

Haugeberg B, Phan J, Liu X, OConnor T, Clift M . Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition. Chem Commun (Camb). 2017; 53(21):3062-3065. PMC: 5604228. DOI: 10.1039/c7cc00485k. View

10.

Burger E, Tunge J . Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives. J Am Chem Soc. 2006; 128(31):10002-3. DOI: 10.1021/ja063115x. View

11.

Wendlandt A, Stahl S . Chemoselective organocatalytic aerobic oxidation of primary amines to secondary imines. Org Lett. 2012; 14(11):2850-3. DOI: 10.1021/ol301095j. View

12.

Zuo Z, MacMillan D . Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore. J Am Chem Soc. 2014; 136(14):5257-60. PMC: 4004246. DOI: 10.1021/ja501621q. View

13.

Kobayashi S, Mori Y, Fossey J, Salter M . Catalytic enantioselective formation of C-C bonds by addition to imines and hydrazones: a ten-year update. Chem Rev. 2011; 111(4):2626-704. DOI: 10.1021/cr100204f. View

14.

Zhang E, Tian H, Xu S, Yu X, Xu Q . Iron-catalyzed direct synthesis of imines from amines or alcohols and amines via aerobic oxidative reactions under air. Org Lett. 2013; 15(11):2704-7. DOI: 10.1021/ol4010118. View

15.

Kobayashi S, Ishitani H . Catalytic enantioselective addition to imines. Chem Rev. 2001; 99(5):1069-94. DOI: 10.1021/cr980414z. View

16.

Beatty J, Stephenson C . Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis. Acc Chem Res. 2015; 48(5):1474-84. PMC: 4440623. DOI: 10.1021/acs.accounts.5b00068. View

17.

Furukawa S, Suga A, Komatsu T . Highly efficient aerobic oxidation of various amines using Pd3Pb intermetallic compounds as catalysts. Chem Commun (Camb). 2014; 50(25):3277-80. DOI: 10.1039/c4cc00024b. View

18.

Wendlandt A, Stahl S . Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst. J Am Chem Soc. 2013; 136(1):506-12. PMC: 3985088. DOI: 10.1021/ja411692v. View

19.

Rueping M, Zhu S, Koenigs R . Visible-light photoredox catalyzed oxidative Strecker reaction. Chem Commun (Camb). 2011; 47(47):12709-11. DOI: 10.1039/c1cc15643h. View

20.

Freeman D, Furst L, Condie A, Stephenson C . Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light. Org Lett. 2011; 14(1):94-7. PMC: 3253246. DOI: 10.1021/ol202883v. View