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Enantioselective catalytic lithiation using a chiral binaphthyl derivative as electron carrier

By Regina Martínez, Isidro M. Pastor and Miguel Yus

Abstract

Dedicated to Prof. Rosa M.ª Claramunt on the occasion of her 65 th birthday The lithiation, of the secondary chloride 2, catalyzed by binaphthyl derivatives, i.e. BINAM 4, BINOL 5, BINAP 6, H8-BINAP 7, Tol-BINAP 8, 2,2’-bis(pyrrolidin-1-yl)-1,1’-binaphthalene 9, and 2,2’-dimethyl-1,1’-binaphthalene 11, in the presence of different ketones has been studied, yielding the corresponding alcohol derivatives 3 and 12-16 in moderate to good yields. Binaphthyl derivative 11 has revealed to be very active as catalyst in the lithiation process at room temperature, and has allowed the preparation of the alcohol derivatives with enantioselectivities up to 50%

Topics: Lithium metal, stereoselectivity, binaphthyl derivatives, arene catalyzed lithiation
Year: 2014
OAI identifier: oai:CiteSeerX.psu:10.1.1.412.4117
Provided by: CiteSeerX
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