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Catalytic Asymmetric Synthesis of 2,2‐Disubstituted Oxetanes from Ketones by Using a One‐Pot Sequential Addition of Sulfur Ylide
Author(s) -
Sone Toshihiko,
Lu Gang,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2009
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/anie.200805473
Subject(s) - ylide , methylene , sulfur , enantiomer , catalysis , chemistry , enantiomeric excess , combinatorial chemistry , organic chemistry , enantioselective synthesis , medicinal chemistry
Better the second time around : The title compounds were synthesized by using a one‐pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme).