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Home > Mathematics and Science Textbooks > Chemistry > Synthesis of Spirolactams Via Phenylseleno Group Transfer Radical Cyclization and Secondary Amine Formation Via Reductive Amination Using Incl3/Et3sih Promoted by Lewis Acid
Synthesis of Spirolactams Via Phenylseleno Group Transfer Radical Cyclization and Secondary Amine Formation Via Reductive Amination Using Incl3/Et3sih Promoted by Lewis Acid

Synthesis of Spirolactams Via Phenylseleno Group Transfer Radical Cyclization and Secondary Amine Formation Via Reductive Amination Using Incl3/Et3sih Promoted by Lewis Acid


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About the Book

This dissertation, "Synthesis of spirolactams via phenylseleno group transfer radical cyclization and secondary amine formation via reductive amination using InCl3/Et3SiH promoted by Lewis acid" by Ka-lun, Law, 羅嘉倫, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Abstract of thesis entitled SYNTHESIS OF SPIROLACTAMS VIA PHENYLSELENO GROUP TRANSFER RADICAL CYCLIZATION AND SECONDARY AMINE FORMATION VIA REDUCTIVE AMINATION USING InCl /Et SiH PROMOTED BY 3 3 LEWIS ACID submitted by Law Ka-Lun for the Degree of Doctor of Philosophy at The University of Hong Kong in July 2007 I. SYNTHESIS OF SPIROLACTAMS VIA PHENYLSELENO GROUP TRANSFER RADICAL CYCLIZATION Phenylseleno group transfer cyclization reactions have been utilized in the synthesis of spirolactam compounds (Scheme 1). The cyclization reactions were performed under simple photolysis conditions at 70-80 C in toluene. Spirolactams with different ring sizes were obtained from the radical cyclization of α-phenylseleno β-ketolactams and α-phenylseleno β-ketoamides in high yields, with moderate regioselectivity and diastereoselectivity (Schemes 2 and 3). The effect of various Lewis acids in the group transfer radical cyclization ireaction was studied. However, Lewis acids only triggered the kinetically favorable O-cyclization reactions of the α-phenylseleno β-ketolactams. The effect of diphenyl diselenide on the group transfer radical cyclization to give spirolactams was studied. The addition of diphenyl diselenide improved the product yield and minimized the formation of side products. Scheme 1 Radical cyclization Radical cyclization O O PhSe Path A Path B SePh α-seleno β-ketolactams O O m n β-ketoamides β-ketolactams Scheme 2 Toluene, UV Cyclization Products Precursors (PhSe), 70-80 C 2.1 2.2 O O O O OO 30 h H H N N + N SePh 99% (2.7:1.5:1) SePh SePh SePh 2.1a 2.2ai 2.2aiii 2.2aii 12 h 75% SePh (1:1) SePh 2.1f 2.2ei: 2.2eii iiScheme 3 Toluene, UV Cyclization Products Precursors (PhSe), 70-80 C 3.1 3.2 O O O 8 h N N H H SePh 99% (5:1) 3.1b SePh SePh 3.2bi 3.2bii 5.5 h SePh 85% (4:1) 3.2fi 3.2fii SePh SePh 3.1f II. SECONDARY AMINE FORMATION VIA REDUCTIVE AMINATION USING InCl /Et SiH PROMOTED BY LEWIS ACID 3 3 A Lewis acid-promoted wide scope reductive amination of aldehydes and ketones to give cyclic, acyclic, aromatic and aliphatic secondary amines using an InCl /Et SiH/MeOH system has been developed (Scheme 4). The advantages of this 3 3 system are its convenience, low toxicity, non-water sensitivity and tolerance of various functional groups. Highly selective formation of secondary amines over tertiary amines was observed, especially when bulky amines, aldehydes or ketones were used. The role of Lewis acids in the direct reductive amination reaction is to activate the in situ generated imine towards reduction. iiiScheme 4 Zn(ClO ) 6H O (0.5 equiv) 4 2 2 InCl (0.3 equiv) 3 R H R H Et SiH (2.0 equiv) R R H 1 2 MeOH, rt 1 equiv 1 equiv H 5.4 5.1 aldehydes 5.3 amines 5.5 5.2 ketones NH


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Product Details
  • ISBN-13: 9781361426517
  • Publisher: Open Dissertation Press
  • Publisher Imprint: Open Dissertation Press
  • Height: 279 mm
  • No of Pages: 484
  • Weight: 1402 gr
  • ISBN-10: 1361426519
  • Publisher Date: 27 Jan 2017
  • Binding: Hardback
  • Language: English
  • Spine Width: 27 mm
  • Width: 216 mm


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Synthesis of Spirolactams Via Phenylseleno Group Transfer Radical Cyclization and Secondary Amine Formation Via Reductive Amination Using Incl3/Et3sih Promoted by Lewis Acid
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