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. Author manuscript; available in PMC: 2012 Dec 7.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Sep 7;50(42):9931–9934. doi: 10.1002/anie.201104726

Scheme 1.

Scheme 1

a) PhI(OAc)2, MeOH, 91%; b) Me2Zn, (S,R,R)-phosphoramidite ligand (4.5% mol%), Cu(OTf)2 (2 mol%), 45–52%; c) LDA; CuCl2, 63%; d) BF3•OEt2, toluene, reflux, 87%; e) Br2, 90%; f) MeI, KOH, 84%; g) aniline, Pd(OAc)2 (8 mol%), [HPt-Bu3][BF4] (11 mol%), NaOt-Bu, toluene, reflux, 93%; h) BBr3; SiO2/air, 62%; i) Pd(OAc)2 (0.5 equiv.), Cu(OAc)2, AcOH, reflux, 33%. OAc = acetate, OTf = trifuoromethane sulfonate, LDA = lithium diisopropylamide, (S,R,R)-phosphoramidite ligand = (S,R,R)-(−)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis(1-phenylethyl)amine.