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 | Zendy

Jörg Swatschek | Zendy; Lydia Grothues | Zendy; Jonathan O. Bauer | Zendy; Carsten Strohmann | Zendy; Mathias Christmann | Zendy

Open Access

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

Author(s) -

Jörg Swatschek,

Lydia Grothues,

Jonathan O. Bauer,

Carsten Strohmann,

Mathias Christmann

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo402422b

Subject(s) - lactone , terpene , chemistry , epoxide , diol , organic chemistry , yield (engineering) , substrate (aquarium) , bifunctional , sex pheromone , transformation (genetics) , stereochemistry , catalysis , materials science , biology , botany , biochemistry , metallurgy , ecology , gene

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.

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