Abstract
The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.
| Original language | English |
|---|---|
| Pages (from-to) | 8370–8375 |
| Number of pages | 6 |
| Journal | Organic Letters |
| Volume | 22 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - 2020 |
| Publication type | A1 Journal article-refereed |
Funding
The Academy of Finland is duly acknowledged for financial support to N.R.C. (Decisions No. 326487 and 326486) and to A. V. (No. 314343). Finnish Cultural Foundation is acknowledged for financial support to S.H. (00190336). CSC–IT Center for Science Ltd., Finland is acknowledged for the allocation of computational resources. Professor Luis F. Veiros (Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Portugal) is acknowledged for fruitful discussions on the computational section.
Publication forum classification
- Publication forum level 2
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 2005907: Experimental Crystal Structure Determination
Holmstedt, S. (Creator), George, L. (Contributor), Koivuporras, A. (Contributor), Valkonen, A. (Contributor) & Candeias, N. R. (Contributor), Cambridge Crystallographic Data Centre, 26 May 2020
DOI: 10.5517/ccdc.csd.cc25b9pj
Dataset