Non‐ C  2 ‐Symmetric, Chirally Economical, and Readily Tunable Linked‐binols: Design and Application in a Direct Catalytic Asymmetric Mannich‐Type Reaction | Zendy

Yoshida Takamasa | Zendy; Morimoto Hiroyuki | Zendy; Kumagai Naoya | Zendy; Matsunaga Shigeki | Zendy; Shibasaki Masakatsu | Zendy

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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.

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