Synthesis of β‐Alkoxy Amines from Alkenes, Sulfonyl Azides, and Alcohols though Copper‐Catalyzed Three‐Component Tandem Reactions via Regioselective Ring‐Opening of Aziridine Intermediates

Abstract

Dedicated to Professor Masahiro Murakami on the occasion of his 65th birthday.

Branching out: redox strategies towards the synthesis of acyclic α-tertiary ethers

“…Tokuyama and Zhao & Zhao exploited this dual catalytic role of copper in recent reports and detailed the synthesis of a small number of a-tertiary ether examples in good to excellent yield. 120,121 In 2017, Duan and Li employed aziridinium ions as reactive intermediates in a one-pot synthesis of valuable prolinol ethers from unfunctionalised olefins (Scheme 27D). 122 This was realised using a combination of NaI and catalytic MnI 2 , under an air atmosphere, to iodinate the double bond with concomitant Scheme 26 Cu-catalysed synthesis of furoindolines and pyrroloindolines from tryptophan derivatives.…”

“…Tokuyama and Zhao & Zhao exploited this dual catalytic role of copper in recent reports and detailed the synthesis of a small number of α-tertiary ether examples in good to excellent yield. 120,121…”

Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane

“…Various methodologies were suggested for their synthesis. − The classical pathway for the synthesis of phenethylamines is the reduction of β-nitrostyrenes (Scheme a) or benzylcyanides . Other synthetic approaches include ring-opening of aryloxiranes with arylamines, nickel-catalyzed alkylative ring-opening of 2-arylaziridines or nickel-photoredox coupling of aryl iodides and aziridines (Scheme b) or copper-catalyzed ring opening of 2-arylaziridines with alcohols, metal- and photocatalyzed hydro- or carboamination of alkenes and alkynes (Scheme c), hydroxyamination of styrenes, reductive amination, as well as alkylation of amines with alkyl halides . Considering that the majority of naturally occurring and synthetic derivatives of phenethylamine 3 (Figure ) ,,, possess an N -methyl group, some of these methods require an additional alkylation step .…”