Application of the Suzuki reaction to the asymmetric desymmetrisation of 1,2-and 1,3-disubstituted bulky cobalt metallocenes

Enda Bergin, David L. Hughes, Christopher J. Richards

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22 Citations (Scopus)

Abstract

Reaction of (eta(5)-cyclopentadienyl)(eta(4)-tetraphenylcyclobutadiene)cobalt with Hg(OAc)(2) (2.3 equiv) in 1:1 MeOH/CH2Cl2 followed by the addition of LiCl resulted in the formation of (eta(5)-1,2-dichloromercuricyclopentadienyl)(eta(4)-tetraphenylcyclobuta diene)cobalt (33%) and its 1,3-isomer (6%). Following conversion into their corresponding diiodides these compounds were desymmetrised by Suzuki reactions with ArB(OH)(2) employing [(R)-BINAP]PdCl2, with the highest ee of 24% being obtained for (eta(5)-1-iodo-3-(2-methoxyphenyl)cyclopentadienyl)(eta(4)-tetraphenylcy clobutadiene)cobalt. (C) 2010 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1619-1623
Number of pages5
JournalTetrahedron: Asymmetry
Volume21
Issue number11-12
DOIs
Publication statusPublished - 2010

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