Tuning the reactivity of O-tert-butyldimethylsilylimidazolyl aminals towards organolithium reagents

Synlett

Volumn , Issue 10, 2003, Pages 1451-1454

  Gimisis, Thanasis ^a   Arsenyan, Pavel ^a,b   Georganakis, Dimitris ^a   Leondiadis, Leondios ^c  

^a UNIVERSITY OF ATHENS   (Greece)

^b LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

^c INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Aldehydes; Brook rearrangements; N,O acetals; Organometallic reagents; Protecting groups

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; IMIDAZOLE DERIVATIVE; ORGANOLITHIUM COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0041568542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40838     Document Type: Article

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36. 3), 125.5 (CH), 135.7 ppm (C).
37. 3), 86.4 (CH), 117.2 (CH), 121.2 (CH), 162.9 ppm (C).
38. 3 at 0 °C, diluted with ethyl acetate, the phases were separated and the organic phase was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude 3a-h was purified by silica gel chromatography. Yields are reported in Table 1.