Non-C2-symmetric, chirally economical, and readily tunable linked-binols: Design and application in a direct catalytic asymmetric mannich-type reaction

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

doi:10.1002/anie.200500425

Non-C₂-symmetric, chirally economical, and readily tunable linked-binols: Design and application in a direct catalytic asymmetric mannich-type reaction

Takamasa Yoshida, Hiroyuki Morimoto, Naoya Kumagai, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journal › Article › peer-review

68 Citations (Scopus)

Abstract

(Chemical Equation Presented) An achiral unit is shown to be better than a chiral unit in promoting an asymmetric reaction. Non-C₂-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 Et₂Zn, the reaction proceeded smoothly to give the product in 98% ee.

Original language	English
Pages (from-to)	3470-3474
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	22
DOIs	https://doi.org/10.1002/anie.200500425
Publication status	Published - 2005 May 30
Externally published	Yes

Keywords

Amino alcohols
Asymmetric catalysis
Chiral ligands
Mannich reaction
Zinc

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.200500425

Cite this

Non-C₂-symmetric, chirally economical, and readily tunable linked-binols : Design and application in a direct catalytic asymmetric mannich-type reaction. / Yoshida, Takamasa; Morimoto, Hiroyuki; Kumagai, Naoya; Matsunaga, Shigeki; Shibasaki, Masakatsu.

In: Angewandte Chemie - International Edition, Vol. 44, No. 22, 30.05.2005, p. 3470-3474.

Research output: Contribution to journal › Article › peer-review

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