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Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with In Situ Generation of Diazocompounds
Author(s) -
Aggarwal Varinder K.,
Alonso Emma,
Hynd George,
Lydon Kevin M.,
Palmer Matthew J.,
Porcelloni Marina,
Studley John R.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010417)40:8<1430::aid-anie1430>3.0.co;2-w
Subject(s) - diazo , catalysis , toluene , chemistry , sulfur , sulfonyl , in situ , stoichiometry , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
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 [Rh 2 (OAc) 4 ] (0.5 mol %).