Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with In Situ Generation of Diazocompounds.
Angew Chem Int Ed Engl, 2001/4/17;40(8):1430-1433.
Aggarwal VK[1], Alonso E[1], Hynd G[1], Lydon KM[1], Palmer MJ[1], Porcelloni M[1], Studley JR[1]
Affiliations
PMID: 29712341DOI: 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO;2-W
Impact factor: 16.823
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 %).
Keywords: asymmetric catalysis; diazo compounds; epoxidation; ylides
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