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

Angewandte Chemie - International Edition

Volumn 44, Issue 22, 2005, Pages 3470-3474

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Amino alcohols; Asymmetric catalysis; Chiral ligands; Mannich reaction; Zinc

Indexed keywords

CATALYSIS; MOLECULAR STRUCTURE; PHENOLS; REACTION KINETICS;

ASYMMETRIC REACTION; BINOLS; CHIRAL UNITS; MANNICH-TYPE REACTION;

CARBON;

LIGAND; MANNICH BASE; NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; LIGANDS; MANNICH BASES; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 20444420552     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500425     Document Type: Article

References (58)

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38. For the synthesis and spectra of ligands 3a-k, see the Supporting Information.
39. The initial reaction rate of the Mannich-type reaction with a meso-linked-binol derivative prepared from (S)-binol and (R)-binol units was estimated relative to that of (S,S)-linked-binol 1a. A similar initial reaction rate was observed for 1a and the meso-linked-binol. The chirality of ligand 3b should be controlled by (S)-biphenol-(S)-binol on complexation with the zinc center because the pseudo-meso-(R)-biphenol-(S)-binol-type complex would afford products in low enantiomeric excess.
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55. [8b]; however, the concentration of 1a had to be > 0.2 mM to promote the reaction efficiently. Under similar conditions given in Scheme 2 ([ligand 1a] = 0.1 mM, 0.01 mol%), TON < 4000.
56. 2Zn/ligand (2:1) would give some insight into the properties of 3c.
57. 2Zn/3c (2:1) are given in the Supporting Information. The ESI mass-spectrometric analysis showed several signals that correspond to the Zn/3c (3:2) trinuclear complex, depending on the natural-isotope distribution pattern of zinc.
58. [8b]