Journal
SYNLETT
Volume -, Issue -, Pages -Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-2047-8456
Keywords
silyllithium; alkenylsilane; allylamine; one-pot synthesis; remote stereocontrol
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The regioselective anti-silyllithiation of propargylic amines provides an efficient route for the synthesis of alkenylsilanes. The reaction involves the formation of a stable alkenyllithium intermediate through intramolecular coordination of the nitrogen functional group. After treatment with an electrophile, the alkenyllithium intermediate is functionalized to yield tetrasubstituted allylic amines bearing a beta-silicon substituent.
The regioselective anti-silyllithiation of propargylic amines is developed to facilitate the efficient synthesis of alkenylsilanes. This reaction generates an alkenyllithium intermediate that is stabilized by the formation of a five-membered cyclic structure through intramolecular coordination of the nitrogen functional group. Upon subsequent treatment with an electrophile, the alkenyllithium intermediate is further functionalized to afford tetrasubstituted allylic amines bearing a beta-sili-con substituent.
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