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Catalytic Asymmetric Mercuriocyclization of γ‐Hydroxy‐ cis ‐Alkenes
Author(s) -
Kang Sung Ho,
Kim Mihyong,
Kang Suk Youn
Publication year - 2004
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.200461289
Subject(s) - enantioselective synthesis , tartrate , catalysis , chemistry , medicinal chemistry , organic chemistry , stereochemistry
2‐Monosubstituted tetrahydrofurans 2 are obtained with 73–95 % ee through the catalytic enantioselective mercuriocyclization of γ‐hydroxy‐( Z )‐alkenes 1 by using Hg(OAc) 2 in the presence of Hg II complexed with tartrate‐derived 4‐(2‐naphthyl)bisoxazoline 3 . The chiral complex was prepared from Hg(tfa) 2 (0.2 equiv) and 3 (0.3 equiv). The amount of MeOH greatly influences the enantioselectivity.