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Application of Chiral Sulfides to Catalytic Asymmetric Aziridination and Cyclopropanation with In Situ Generation of the Diazo Compound
Author(s) -
Aggarwal Varinder K.,
Alonso Emma,
Fang Guangyu,
Ferrara Marco,
Hynd George,
Porcelloni Marina
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<1433::aid-anie1433>3.0.co;2-e
Subject(s) - cyclopropanation , diazo , catalysis , chemistry , sulfide , yield (engineering) , sulfonyl , enantioselective synthesis , toluene , organic chemistry , combinatorial chemistry , materials science , alkyl , metallurgy
Imines and alkenes can be converted into the corresponding aziridines and cyclopropanes (see scheme, PTC=phase‐transfer catalyst, Ts=toluene‐4‐sulfonyl) in good yield with moderate to high d.r. and high ee values using tosylhydrazone salts with catalytic quantities of chiral sulfide (5–20 mol %) and metal catalyst (1 mol %). The process is particularly suited to the synthesis of conformationally locked cyclopropyl amino acids, which can now be prepared in only three steps from commercially available material in 100 % ee.