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Synthesis of α-propargylglycinates using the borono-mannich reaction with pinacol allenylboronate and potassium allenyltrifluoroborate

Journal Article


Abstract


  • The three component borono-Mannich reactions of ethyl glyoxylate, primary or secondary amines and pinacol allenylboronate or potassium allenyltrifluoroborate are highly regioselective and give α-propargylglycinates. The (S)-N-tert-butylsulfinyl imine of ethyl glyoxylate underwent an indium chloride catalyzed addition reaction with allenyl potassium trifluoroborate in a highly regioselective and diastereoselective manner to give ethyl (S)-α-propargylglycinate after N-deprotection in 97 % ee.

UOW Authors


  •   Chambers, Rachel K. (external author)
  •   Chaipukdee, Nattapong (external author)
  •   Thaima, Thanaphat (external author)
  •   Kanokmedhakul, Kwanjai (external author)
  •   Pyne, Stephen

Publication Date


  • 2016

Citation


  • Chambers, R. K., Chaipukdee, N., Thaima, T., Kanokmedhakul, K. & Pyne, S. G. (2016). Synthesis of α-propargylglycinates using the borono-mannich reaction with pinacol allenylboronate and potassium allenyltrifluoroborate. European Journal of Organic Chemistry, 2016 (22), 3765-3772.

Scopus Eid


  • 2-s2.0-84978428097

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4144

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3765

End Page


  • 3772

Volume


  • 2016

Issue


  • 22

Place Of Publication


  • Germany

Abstract


  • The three component borono-Mannich reactions of ethyl glyoxylate, primary or secondary amines and pinacol allenylboronate or potassium allenyltrifluoroborate are highly regioselective and give α-propargylglycinates. The (S)-N-tert-butylsulfinyl imine of ethyl glyoxylate underwent an indium chloride catalyzed addition reaction with allenyl potassium trifluoroborate in a highly regioselective and diastereoselective manner to give ethyl (S)-α-propargylglycinate after N-deprotection in 97 % ee.

UOW Authors


  •   Chambers, Rachel K. (external author)
  •   Chaipukdee, Nattapong (external author)
  •   Thaima, Thanaphat (external author)
  •   Kanokmedhakul, Kwanjai (external author)
  •   Pyne, Stephen

Publication Date


  • 2016

Citation


  • Chambers, R. K., Chaipukdee, N., Thaima, T., Kanokmedhakul, K. & Pyne, S. G. (2016). Synthesis of α-propargylglycinates using the borono-mannich reaction with pinacol allenylboronate and potassium allenyltrifluoroborate. European Journal of Organic Chemistry, 2016 (22), 3765-3772.

Scopus Eid


  • 2-s2.0-84978428097

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/4144

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3765

End Page


  • 3772

Volume


  • 2016

Issue


  • 22

Place Of Publication


  • Germany