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Stereocontrolled Synthesis of (11 Z )‐Retinal and Its Analogues
Author(s) -
Uenishi Jun'ichi,
Kawahama Reiko,
Yonemitsu Osamu,
Wada Akimori,
Ito Masayoshi
Publication year - 1998
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/(sici)1521-3773(19980216)37:3<320::aid-anie320>3.0.co;2-4
Subject(s) - suzuki reaction , retinal , catalysis , chemistry , combinatorial chemistry , benzene , stereochemistry , organic chemistry , biochemistry , palladium
Suzuki coupling of stereochemically pure ( Z )‐bromotetraene 1 —which is extremely unstable but can be kept in frozen benzene in the presence of a small amount of PPh 3 at &sminus 01;20°C—and ( Z )‐alkenylboronic acid 2 provides the stereocontrolled synthesis of (11 Z )‐retinal 3 . The 11 Z configuration, which is introduced by selective catalytic debromination of the corresponding dibromo precursor of 1 , is retained in this step. TBDMS = t BuMe 2 Si.