Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1725-1729

  Merino, Pedro ^a   Castillo, Elena ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE; POLYOL; REAGENT;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030996035     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00175-4     Document Type: Article

References (44)

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40. D +1.2.
41. 3) data. 17a: δ -0.23 (s, 3H), -0.16 (s, 3H), 0.74 (s, 9H), 3.21 (dd, 1H, J=10.7, 6.6 Hz), 3.50 (dd, 1H, J=10.7, 5.7 Hz), 3.60 (d, 1H, J=14.5 Hz), 4.55 (d, 1H, J=8.3 Hz), 4.65 (ddd, 1H, J=8.3, 6.6, 5.7 Hz), 4.90 (d, 1H, J=14.5 Hz), 7.10-7.37 (m, 10H). 17b: δ -0.22 (s, 3H), -0.14 (s, 3H), 0.78 (s, 9H), 3.64 (d, 1H, J=14.5 Hz), 3.64 (dd, 1H, J=11.5, 3.3 Hz), 3.76 (dd, 1H, J=11.5, 4.2 Hz), 4.27 (ddd, 1H, J=6.4, 4.2, 3.3 Hz), 4.47 (d, 1H, J=6.4 Hz), 4.87 (d, 1H, J=14.5 Hz), 7.12-7.36 (m, 10H). 18a: δ -0.01 (s, 3H), 0.00 (s, 3H), 0.81 (s, 9H), 1.22 (d, 3H, J=6.4 Hz), 3.74 (dq, 1H, J=8.2, 6.4 Hz), 3.80 (m, 2H), 4.07 (d, 1H, J=15.1 Hz), 4.40 (pseudo dt, 1H, J=8.2, 5.5 Hz), 4.78 (d, 1H, J=15.1 Hz), 7.24-7.33 (m, 5H). 18b: δ -0.01 (s, 3H), 0.01 (s, 3H), 0.81 (s, 9H), 1.23 (d, 3H, J=6.3 Hz), 3.56 (dq, 1H, J=6.3, 6.3 Hz), 3.68 (m, 2H), 4.00 (dt, 1H, J=6.3, 4.3), 4.08 (d, 1H, J=15.3 Hz), 4.75 (d, 1H, J=15.3 Hz), 7.22-7.35 (m, 5H). 19a: δ -0.03 (s, 3H), -0.01 (s, 3H), 0.81 (s, 9H), 0.83 (t (3H, J=7.3 Hz), 1.60 (m, 2H), 3.57 (ddd, 1H, J=7.6, 4.1, 2.6 Hz), 3.84 (m, 2H), 4.05 (d, 1H, J=15.0 Hz), 4.43 (dt, 1H, J=5.2, 7.6 Hz), 4.78 (d, 1H, J=15.0 Hz), 7.24-7.35 (m, 5H). 19b: δ -0.03 (s, 3H), -0.01 (s, 3H), 0.81 (s, 9H), 0.90 (t, 3H, J=7.3 Hz), 1.50 (m, 2H), 3.45 (ddd, 1H, J=7.6, 4.6, 3.2 Hz), 3.62 (m, 2H), 4.03 (d, 1H, J=15.0 Hz), 4.14 (pseudo quintuplet, 1H, J=4.6 Hz), 4.79 (d, 1H, J=15.0 Hz), 7.24-7.35 (m, 5H).
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44. Merchan, F.L.; Merino, P.; Tejero, T. The Molecular Modelling Electronic Conference. (TMMeC-1). Ventura, O.N.; Cachau, R.E. (Eds.). Montevideo Theoretical Chemistry Laboratory. Universidad de la Republica. Montevideo (Uruguay). 1995. Internet: http://uqbar.ncifcrf.gov/agora/