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A Straightforward Synthesis of Trideuterated α‐Terpinene for Mechanistic Studies
Author(s) -
Mitschke Nico,
Christoffers Jens,
Wilkes Heinz
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000684
Subject(s) - chemistry , isopropyl , enol , deuterium , yield (engineering) , lithium (medication) , alkyl , coupling reaction , stereochemistry , combinatorial chemistry , organic chemistry , medicine , physics , materials science , quantum mechanics , metallurgy , endocrinology , catalysis
Regiospecifically trideuterated (2,6,6‐ 2 H 3 )‐α‐terpinene was prepared in six steps and with a deuterium incorporation of >99 % in 24 % yield from 1,4‐cyclohexanedione monoethylene ketal. The synthetic procedure involved twofold cross‐coupling reactions of alkylcuprates (lithium dimethylcuprate and chloromagnesium cyano(isopropyl)cuprate, respectively) with enol triflates to introduce the alkyl substituents on the 1,3‐cyclohexadiene backbone. By changing the alkylcuprates, the synthetic approach could serve as a prototype for the synthesis of various 1,4‐dialkyl‐substituted 1,3‐cyclohexadiene derivatives, which could be deuterium‐labeled as well, for example for mechanistic studies.