Diastereoselectivity control in the TiCl4-mediated addition reaction of allyltrimethylsilane to N,O-protected (L)-serinals

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9835-9838

  Jurczak, Janusz ^a,b   Prokopowicz, Piotr ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE DERIVATIVE; SILANE DERIVATIVE; TITANIUM; TITANIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0032564562     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02245-X     Document Type: Article

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17. 2 column with a mixture of n-bexane and isopropanol (97.5:2.5 v/v) as eluent.
18. 12 Relative configurations of adducts formed in other reactions were established on the basis of their chemical correlations with syn-6 and anti-7.
19. 2=3.3 Hz, 1H), 3.66-3.60 (m, 2H), 3.60-3.50 (m, 2H), 2.12-2.05 (m, 2H), 0.80 (s, 9H), -0.08 (s, 6H).
20. 3=10.3 Hz, 1H), 4.95 (s, 2H), 4.93-4.85 (m, 4H), 4.39 (s, 2H), 4.32 (s, 2H), 3.67-3.46 (m, 4H), 2.12-2.04 (m, 2H).
21. 8, δ): 7.19-6.89 (m, 10H), 5.81-5.67 (m, 1H), 4.98 (s, 1H), 4.97 (s, 1H), 4.90 (m, 1H), 4.86 (s, 1H), 4.56 (d, J=15.6 Hz, 1H), 4.48 (d, J=15.6 Hz, 1H), 3.89-3.75 (m, 3H), 3.73-3.62 (m, 2H), 2.11-2.03 (m, 2H), 0.81 (s, 9H), -0.10 (s, 6H).
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24. 2=4.0 Hz, 1H), 3.89 (m, 1H), 3.76-3.65 (m, 1H), 2.14 (m, 2H).