Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines to allyl alcohol utilizing tartaric acid ester as a chiral auxiliary

Heterocycles

Volumn 80, Issue 2, 2010, Pages 887-893

  Tanaka, Katsuyoshi ^a   Kato, Tomomitsu ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Azomethine Imine; Diisopropyl(R,R) Tartrate; Enantioselective 1,3 Dipolar Cycloaddition; Magnesium Bromide; Optically Active Pyrazolidine

Indexed keywords

EID: 77953665800     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)116     Document Type: Article

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31. Magnesium bromide was generated in situ by the treatment of magnesium metal with 1,2-dibromoethane in THF.
32. The cycloaddition in the absence of MgBr2 in MeCN once gave 3a in 52% yield with 63% ee. However, in the worst case, 3a was produced in 66% yield with 35% ee.
33. 2: 17%/85% ee.
34. By comparison of the results between from the reaction of 1.0 mmol scale of 2 in 6 ml EtCN and from the reaction of 0.5 mmol scale of 2 in 6 ml EtCN, the better results are listed in Table 3.
35. By-product 4 might be produced by 1,3-dipolar cycloaddition of 2d to an enamine-type tautomer of 2d generated in situ.
36. The 1,3-dipolar cycloaddition of 2a to ally benzyl ether did not proceed at all under similar reaction conditions. The generation of chloromagnesium salt of allyl alcohol (1) (B) was crucial for the present reaction.
37. A background reaction in the absence of chloromagnesium salt of (R,R)-DIPT gave racemic 3a in 65% yield under the similar conditions.