Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)–H Functionalization
- 10 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (19), 7359-7363
- https://doi.org/10.1021/acs.orglett.1c02513
Abstract
A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereo-specific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.Keywords
Funding Information
- National Natural Science Foundation of China (21772024, 21921003, 22071028)
This publication has 39 references indexed in Scilit:
- Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H2 HydrogenationJournal of the American Chemical Society, 2011
- Iridium-Catalyzed Arene Ortho-Silylation by Formal Hydroxyl-Directed C−H ActivationJournal of the American Chemical Society, 2010
- Iridium-Catalyzed, Silyl-Directed Borylation of Nitrogen-Containing HeterocyclesJournal of the American Chemical Society, 2010
- CuH-Catalyzed ReactionsChemical Reviews, 2008
- Russujaponols A−F, Illudoid Sesquiterpenes from the Fruiting Body of Russula japonicaJournal of Natural Products, 2006
- Synthesis of Optically Pure (+)-Puraquinonic Acid and Assignment of Absolute Configuration to Natural (−)-Puraquinonic Acid. Use of Radical Cyclization for Asymmetric Generation of a Quaternary CenterThe Journal of Organic Chemistry, 2004
- Synthesis of (±)-Puraquinonic Acid: An Inducer of Cell DifferentiationThe Journal of Organic Chemistry, 2001
- The Sesquiterpenoid Contents of Fruit Bodies of Russula delica.Acta Chemica Scandinavica, 1998
- Puraquinonic Acid, a Novel Inducer of Differentiation of Human HL-60 Promyelocytic Leukemia Cells fromMycena pura(Pers. Ex Fr.)Natural Product Letters, 1997
- A new method for the deoxygenation of secondary alcoholsJournal of the Chemical Society, Perkin Transactions 1, 1975