A Formal, One-Pot beta-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C-2-Symmetrical Terminal Bis-Epoxide

作者：Swatschek Joerg; Grothues Lydia; Bauer Jonathan O; Strohmann Carsten; Christmann Mathias^*

来源：Journal of Organic Chemistry, 2014, 79(3): 976-983.

DOI：10.1021/jo402422b

A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.

• 出版日期2014-2-7