Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.
Regioselective, stereoselective: The convergent coupling of allylic alcohols with imines to deliver stereodefined homoallylic amines is described (see scheme). The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity.
Takahashi
Masayuki
M
Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way 3A2, Jupiter, FL 33458, USA.
McLaughlin
Martin
M
Micalizio
Glenn C
GC
D007097:Imines / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
D007097:Imines; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D014025:Titanium; D008274:Magnesium