Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
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DOI：
10.1039/c6sc03036j
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发表时间：
2017-01-01
期刊：
影响因子：
8.4
通讯作者：
Marek, Ilan
中科院分区：
文献类型：
--
作者：
Nairoukh, Zackaria;Kumar, Gunda G. K. S. Narayana;Marek, Ilan
一系列区域和立体选择性的碳金属化，然后是ynamide的氧化，导致了立体定义的全取代烯醇酸酯，随后与各种官能化的烯丙基溴试剂反应，在恶唑烷酮部分被裂解后，以极好的产率和对映体比提供预期的产物，该产物具有具有α位置的对映体纯的季碳立体中心到羰基。三种新债券是在一次单一的操作中形成的。
A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carbon stereocentre in the alpha-position to the carbonyl group in excellent yields and enantiomeric ratios after cleavage of the oxazolidinone moiety. Three new bonds are formed in a single-pot operation.