Asymmetric Strecker reaction of ketoimines catalyzed by a novel chiral bifunctional N,N′-dioxide

Advanced Synthesis and Catalysis

Volumn 348, Issue 18, 2006, Pages 2579-2584

  Huang, Xiao ^a   Huang, Jinglun ^a   Wen, Yuehong ^a   Feng, Xiaoming ^a,b  

^a Sichuan University   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Ketoimines; Organocatalyst; Strecker reaction

Indexed keywords

EID: 33846016222     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600238     Document Type: Article

References (48)

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45. There should be an equilibrium between TMSCN and HCN in the presence of phenol, and it is TMSCN, not HCN, combined with the N,N-dioxide that could generate a highly reactive cyanating agent. To support this hypothesis we have done the following experiment: Method I: To a stirred solution of 1a (27.3 mg, 0.1 mmol) and B1 (3.6 mg, 0.01 mmol, 10 mol%) in 0.5 mL toluene, ethyl cyanoformate (20 μL, 2 equivs.) was added in one portion at ambient temperature, followed by addition of acetic acid (12 μL, 2 equivs.). Method II: To a stirred solution of 1a (27.3 mg, 0.1 mmol) and B1 (3.6 mg, 0.01 mmol, 10 mol%) in 0.5 mL water-saturated toluene, ethyl cyanoformate (20 μL, 2 equivs.) was added in one portion at ambient temperature. These two methods are alternative ways instead of using TMSCN and phenol that could produce HCN which could serve as cyanating agent. As predicted, after 30 h stirring at ambient temperature, no product was detected (by TLC) for both methods. This could demonstrate that the silicon reagent plays an important role in the present catalytic system and TMSCN is very likely to be the real cyanating agent. Or we may suggest that a highly reactive intermediate might be generated by combination of TMSCN and N,N-dioxide. Comparably, there is no such interaction between HCN and N,N-dioxide with the result that no addition occurred.
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