Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes.

Autor: Kuhwald C; Institute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany., Kirschning A; Institute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2021 Jun 04; Vol. 23 (11), pp. 4300-4304. Date of Electronic Publication: 2021 May 13.
DOI: 10.1021/acs.orglett.1c01222
Abstrakt: The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative workup. The new terpene alcohols are validated with respect to their olfactoric properties.
Databáze: MEDLINE