A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

作者：Slobodyanyuk Evgeniy Y; Artamonov Oleksiy S; Kulik Irene B; Rusanov Eduard; Volochnyuk Dmitriy M; Grygorenko Oleksandr O^*

来源：Heterocyclic Communications, 2018, 24(1): 11-17.

DOI：10.1515/hc-2017-0235

• conformational restriction
• heteroaliphatic
• lead-oriented synthesis
• oxazoles
• peptidomimetics
• synthesis

A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from L-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides - aldehyde intermediates which demonstrate low to moderate stability - under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17-51% overall yield and has been used at up to a 45-g scale.

• 出版日期2018-2