Title

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

RIS ID

109752

Publication Details

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.

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.

Please refer to publisher version or contact your library.

Share

COinS
 

Link to publisher version (DOI)

http://dx.doi.org/10.1002/ejoc.201600436