Iterative Synthesis of Polydeoxypropionates Based on Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted Acrylic Acids

作者：Che, Wen; Wen, Danyang C.; Zhu, Shou-Fei^*; Zhou, Qi-Lin^*

来源：Organic Letters, 2018, 20(11): 3305-3309.

DOI：10.1021/acs.orglett.8b01193

• MYCOBACTERIUM-TUBERCULOSIS
• ENANTIOSELECTIVE SYNTHESIS
• STEREOSELECTIVE-SYNTHESIS
• SELECTIVE SYNTHESIS
• CONJUGATE ADDITION
• PHTHIOCERANIC ACID
• EFFICIENT
• CARBOALUMINATION
• CONVERGENT
• BORRELIDIN

A novel iterative protocol for the synthesis of polydeoxypropionates was developed based on iridium-catalyzed asymmetric hydrogenation of alpha-substituted acrylic acids. The catalyst loading can be as low as 0.01 mol %, and the overall yield for one iterative cycle is >76%. The reaction conditions are mild, and no organometallic reagents or chromatography steps are required. Using this protocol, (+)-phthioceranic acid and the polydeoxypropionate motifs of ionomycin and borrelidin were synthesized in high yield.

• 出版日期2018-6-1
• 单位南开大学