Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with In Situ Generation of Diazocompounds
- 17 April 2001
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 40 (8) , 1430-1433
- https://doi.org/10.1002/1521-3773(20010417)40:8<1430::aid-anie1430>3.0.co;2-w
Abstract
A practical, general, and convergent route to epoxides with control of the relative and absolute stereochemistry has been achieved by generating the reactive intermediate (the diazo compound) in situ from tosylhydrazone salts (see scheme, PTC=phase-transfer catalyst, Ts=toluene-4-sulfonyl). High yields (58–82 %), high d.r. (88:12–98:2), and high ee values (87–94 %) have been obtained using a new class of stable chiral sulfides at low catalyst loading (5 mol %) and [Rh2(OAc)4] (0.5 mol %).This publication has 15 references indexed in Scilit:
- A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone saltsTetrahedron Letters, 2000
- A Simple Method for the Synthesis of Substituted Benzylic Ketones: Homologation of Aldehydes via the in Situ Generation of Aryldiazomethanes from Aromatic AldehydesThe Journal of Organic Chemistry, 2000
- Comprehensive Asymmetric Catalysis I–IIIPublished by Springer Nature ,1999
- Catalytic Asymmetric Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in Sulfur Ylide Epoxidations with Chiral 1,3-OxathianesJournal of the American Chemical Society, 1998
- Catalytic Asymmetric Epoxidation and Aziridination Mediated by Sulfur Ylides. Evolution of a ProjectSynlett, 1998
- Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and RearrangementChemical Reviews, 1997
- Direct Asymmetric Epoxidation of Aldehydes Using Catalytic Amounts of Enantiomerically Pure SulfidesJournal of the American Chemical Society, 1996
- Thioaldehyde Diels-Alder reactionsThe Journal of Organic Chemistry, 1986
- A Simple Method for Generation of Diazocompounds in an Aqueous Two-Phase SystemSynthetic Communications, 1978
- 924. The decomposition of toluene-p-sulphonylhydrazones by alkaliJournal of the Chemical Society, 1952