Highly stereoselective addition of stannylcuprates to alkynones

Thomas Eiland Nielsen, M.A.C. de Dios, David Ackland Tanner

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Abstract

The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.
Original languageEnglish
JournalJournal of organic chemistry
Volume67
Issue number21
Pages (from-to)7309-7313
ISSN0022-3263
Publication statusPublished - 2002

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