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 language | English |
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| Journal | Journal of organic chemistry |
| Volume | 67 |
| Issue number | 21 |
| Pages (from-to) | 7309-7313 |
| ISSN | 0022-3263 |
| Publication status | Published - 2002 |