On the mechanism of stereoselection in direct Mannich reaction catalyzed by BINOL-derived phosphoric acids

Tetrahedron Letters

Volumn 48, Issue 3, 2007, Pages 497-500

  Gridnev, Ilya D ^a   Kouchi, Mitsuhiro ^a   Sorimachi, Keiichi ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; IMINE; PHOSPHORIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MANNICH REACTION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 33845454140     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.017     Document Type: Article

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45. We have also regarded the possibility of 2:1 adducts, and have optimized corresponding structures (see ESI for details). However, the participation of such species in the stereoselective catalytic cycle is excluded since we have found linear dependence of the product ee versus catalyst ee in the reaction of Eq. 1.
46. We also tried to locate another structure corresponding to the coordination of cis-2a with different chiral phosphoric acid applied for the computations (see ESI for details). However, results were very similar to those for 4a-c: apparently the alternative mode of the cis-imine coordination is destabilized due to unfavourable closeness of the t-Bu substituent of imine and one of the bulky radicals of the phosphoric acid.
47. 2 (see Ref. 5a).
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49. The present analysis demonstrating how the asymmetric pocket for the enantioselective nucleophilic attack is being created opens the door for the computation of transition states involving nucleophile that are necessary to allow more confident conclusions on the mechanism of enantioselection.