Catalytic asymmetric protonation of α-amino acid-derived ketene disilyl acetals using P -Spiro diaminodioxaphosphonium barfates as chiral proton

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12240-12242

  Uraguchi, Daisuke ^a   Kinoshita, Natsuko ^a   Ooi, Takashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE;

AMINO ACIDS; PROTONATION; PROTONS;

ORGANIC ACIDS;

4 SPIRODIAMINODIOXAPHOSPHONIUM BARFATE; ALPHA AMINO ACID; KETENE DERIVATIVE; PHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

APTITUDE; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; PROTON TRANSPORT;

ACETALS; AMINO ACIDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ESTERS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PROTONS; SILANES;

EID: 77956241458     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja105945z     Document Type: Article

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35. a = 12.53) (20)
36. The addition of 5 is preferable in order to reproduce the high enantioselectivity, presumably because it avoids the influence of the non-enantioselective background reaction by the liberated HBArF.
37. Under catalytic conditions, use of sterically rather demanding 2,6-dimethylphenol as a stoichiometric proton source seems to be important in order to realize the full potential of 1 as a chiral proton, judging from the fact that replacement of 2,6-dimethylphenol with phenol in the 1c HBArF-catalyzed protonation of 3a under conditions otherwise identical to the optimized conditions afforded 4a quantitatively with 94% ee. The observed decrease in enantioselectivity might suggest the intervention of either a different mechanism or non-stereoselective protonation by phenol.
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