Abstract
On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.
Original language | English |
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Pages (from-to) | 5442-5445 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 12 |
Issue number | 23 |
Early online date | 9 Nov 2010 |
DOIs | |
Publication status | Published - 3 Dec 2010 |