A formal, one-pot β-chlorination of primary alcohols and its utilization in the transformation of terpene feedstock and the synthesis of a C2-symmetrical terminal bis-epoxide.
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.
Institute of Chemistry and Biochemistry, Organic Chemistry, Freie Universität Berlin , Takustrasse 3, 14195 Berlin, Germany.
Jörg
J
Swatschek
Lydia
L
Grothues
Jonathan O
JO
Bauer
Carsten
C
Strohmann
Mathias
M
Christmann
D000438:Alcohols / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D013729:Terpenes