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Non‐ C 2 ‐Symmetric, Chirally Economical, and Readily Tunable Linked‐binols: Design and Application in a Direct Catalytic Asymmetric Mannich‐Type Reaction
Author(s) -
Yoshida Takamasa,
Morimoto Hiroyuki,
Kumagai Naoya,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2005
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.200500425
Subject(s) - catalysis , unit (ring theory) , ligand (biochemistry) , type (biology) , chemistry , product (mathematics) , scheme (mathematics) , mannich reaction , combinatorial chemistry , stereochemistry , medicinal chemistry , computer science , organic chemistry , mathematics , biology , ecology , mathematical analysis , biochemistry , receptor , mathematics education , geometry
An achiral unit is shown to be better than a chiral unit in promoting an asymmetric reaction. Non‐ C 2 ‐symmetric linked‐binols 1 with one chiral 1,1′‐bi‐2‐naphthol unit and one flexible achiral unit are employed as ligands in direct catalytic asymmetric Mannich‐type reactions (see scheme; TON=turnover number). With as little as 0.01 mol % of ligand 1 a and 0.04 mol % of Et 2 Zn, the reaction proceeded smoothly to give the product in 98 % ee.