Details
| Original language | English |
|---|---|
| Pages (from-to) | 4300–4304 |
| Number of pages | 5 |
| Journal | Organic letters |
| Volume | 23 |
| Issue number | 11 |
| Early online date | 13 May 2021 |
| Publication status | Published - 4 Jun 2021 |
Abstract
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 23, No. 11, 04.06.2021, p. 4300–4304.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Matteson Reaction under Flow Conditions
T2 - Iterative Homologations of Terpenes
AU - Kuhwald, Conrad
AU - Kirschning, Andreas
N1 - Funding Information: We thank the Alexander-von-Humboldt Foundation for financial support and Dr. M. Norris as well as Dr. J. Panten (Symrise AG, Holzminden, Germany) for helpful discussions and technical advice. We thank Allychem Co. Ltd. for donation of chemicals.
PY - 2021/6/4
Y1 - 2021/6/4
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85106378878&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.1c01222
DO - 10.1021/acs.orglett.1c01222
M3 - Article
C2 - 33983747
AN - SCOPUS:85106378878
VL - 23
SP - 4300
EP - 4304
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 11
ER -