Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2

Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2
Li−Li Liao, Zhen Zhang, Yong-Yuan Gui, Naifu Hu, Tao Ju, Xiao-Wang Chen, Jing Li, Da-Gang Yu, Jian-Heng Ye
Herein, we report a highly regio- and enantioselective copper-catalyzed reductive hydroxymethylation of styrenes and 1,3-dienes with 1 atm of CO2. Diverse important chiral homobenzylic alcohols were readily prepared from styrenes. Moreover, a variety of 1,3-dienes also were converted to chiral homoallylic alcohols with high yields and excellent regio-, enantio-, and Z/E-selectivities. The utility of this transformation was demonstrated by a broad range of styrenes and 1,3-dienes, facile product modification, and synthesis of bioactive compounds (R)-(−)-curcumene and (S)-(+)-ibuprofen. Mechanistic studies demonstrated the carboxylation of phenylethylcopper complexes with CO2 as one key step.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b10149

DOI: 10.1021/jacs.7b10149

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