Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Oleksandr O. Grygorenko; Maksym Kurkunov; Igor A. Levandovskiy; Andriy V. Tymtsunik

doi:10.1055/s-0037-1609434

Synthesis, Table of Contents

Synthesis 2018; 50(10): 1973-1978
DOI: 10.1055/s-0037-1609434

paper

Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Oleksandr O. Grygorenko *

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine

^bTaras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine Email: gregor@univ.kiev.ua

,

Maksym Kurkunov

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine

,

Igor A. Levandovskiy

^cNational Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine

,

Andriy V. Tymtsunik

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine

^cNational Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine

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Abstract

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Abstract

An approach to 2-azabicyclo[n.2.0]alkane derivatives (n = 1, 2), which relies on a tandem Strecker reaction–intramolecular nucleophilic cyclization (STRINC) sequence of the corresponding 2-(ω-chloroalkyl)cyclobutanones (in turn prepared by [2+2] cycloaddition of keteniminium salts and ethylene) is described. The utility of the method is demonstrated by multigram syntheses of bicyclic proline analogues, monoprotected diamines, as well as parent 2-azabicyclo[4.2.0]octane.

Key words

cycloaddition - bicyclic compounds - amino acids - conformational restriction - cyclobutanes - nitrogen heterocycles - keteniminium salts - Strecker reaction

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References

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