Diastereoselective hydrocyanation of chiral nitrones. Synthesis of novel α-(Hydroxyamino) nitriles

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 9028-9032

  Merino, P ^a   Lanaspa, A ^a   Merchan, F L ^a   Tejero, T ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000813467     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961293a     Document Type: Article

References (63)

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53. O-(Trimethylsilyl) derivatives can be readily transformed into the α-(hydroxyamino) nitriles by treatment with 4 p/v methanolic citric acid at room temperature.
54. In our previous paper (see ref 17) we reported a reversed selectivity for these conditions. After several repetitions we were unable to obtain our previously reported result.
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58. Compounds 11 and 13 could not be separated, and they were isolated and characterized as the corresponding a-(hydroxyamino) nitriles 12 and 14, respectively. In addition, compounds anti-lGb and anti-17b could not be isolated as single diastereoisomers.
59. The authors have deposited atomic coordinates, bond lengths, and angles for structures anti-10b, anti-lib, anti-13b, and syn-18a with the Cambridge Crystallographic Data Centre. The data can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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