Highly 2,3-trans stereoselective allylations of 2, 3-O-isopropylidene-protected pyrrolidines: circumventing the N-acyliminium ion chemistry?
[reaction: see text] A remarkable exo-facial template effect exercised by a 2, 3-O-isopropylidene protective group is the key for the entire 2, 3-trans stereoselectivity observed in the allylsilane addition promoted by BF(3).OEt(2) to 2,3-O-isopropylidene-protected pyrrolidines.
de Armas
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P
Instituto de Productos Naturales y Agrobiología-CSIC, Astrofísico Francisco Sánchez 3, 38206 La Laguna-Tenerife, Spain. parmas@ipna.csic.es
García-Tellado
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F
Marrero-Tellado
J J
JJ
D015195:Drug Design; D007097:Imines; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007097:Imines; D007202:Indicators and Reagents; D011759:Pyrrolidines