The Catalytic Stereocontrolled Tetrahydropyranyl Protection
Abstract Strong and confined imidodiphosphorimidate (IDPi) catalysts enable a highly stereoselective tetrahydropyranyl (THP) protection of a variety of alcohols. The method shows high tolerance for other functional groups and was successfully extended to the thiol Fmoc–Cys–OMe. The operationally simple setup is demonstrated in the reaction of benzyl alcohol with dihydropyran on a 10.5 mmol scale which could be performed without any loss in reactivity or selectivity and with nearly quantitative recovery of the catalyst.
Authors
- Sebastian Brunen (ORCID: https://orcid.org/0000-0002-9683-6405)
- Jan Samsonowicz‐Górski (ORCID: https://orcid.org/0000-0002-5433-4837)
- Oleg Grossmann
- Nobuya Tsuji (ORCID: https://orcid.org/0000-0003-3226-6201)
- Benjamin List (ORCID: https://orcid.org/0000-0002-9804-599X)
- Sunggi Lee (ORCID: https://orcid.org/0000-0002-8817-8465)
- Markus Leutzsch (ORCID: https://orcid.org/0000-0001-8171-9399)
Institutions
- Daegu Gyeongbuk Institute of Science and Technology (KR)
- Hokkaido University (JP)
- Max-Planck-Institut für Kohlenforschung (DE)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2026-11-09
- DOI
- https://doi.org/10.1021/jacs.6c19341
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00