NOVEL APPROACH TO SATURATED AMINO ACID DERIVATIVES WITH ISOLATED (HETERO)CYCLIC RINGS <i>via</i> THE HYDROGENATION OF DIENES

Authors

  • Eduard V. Verner Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine
  • Bohdan V. Vashchenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Bohdan V. Sosunovych Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine
  • Andriy I. Frolov Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine
  • Vladyslav V. Subotin Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine
  • Andriy Kozytskiy Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine
  • Oleksandr O. Grygorenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Sergey V. Ryabukhin Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Dmitriy M. Volochnyuk Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02096, Ukraine
  • Sergey V. Kolotilov Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine

DOI:

https://doi.org/10.1007/7723

Keywords:

amino acids, dienes, building blocks, diene reduction, isolated cycles, Suzuki coupling.

Abstract

Synthesis of amino acids with isolated saturated (hetero)carbocyclic scaffold was disclosed. The method relied on Suzuki cross-coupling reaction of heteroacycloalkene triflates and N-Boc-tetrahydropyridine boron pinacolates followed by catalytic hydrogenation of the conjugated dienes thus obtained, which proceeded with good diastereoselectivity for scaffolds with two six-membered cycles and low diastereoselectivity for a five-membered analog. Several amino acid derivatives have also been obtained, i.e. amino esters, NH- and N-Boc-substituted amino acids – promising building blocks for medicinal and synthetic chemistry.

Author Biography

Sergey V. Kolotilov, Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine

L.V. Pisarzhevskii Institute of Physical Chemistry of the National Academy of Sciences of Ukraine, Deputy director on scientific work

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers