Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes
Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes
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DOI：
10.1021/ja068723r
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发表时间：
2007-03-14
影响因子：
15
通讯作者：
Toste, F. Dean
中科院分区：
文献类型：
--
作者：
Corkey, Britton K.;Toste, F. Dean
描述了甲硅烷基烯醇醚和甲硅烷基乙烯酮缩醛胺在炔烃上的对映选择性分子内加成。该反应采用 DTBMSegphos-Pd(II) 或 Binaphane-Pd(II) 络合物作为催化剂，由 1,6-烯炔前体形成亚甲基环戊烷加合物。该反应的实用性通过其在细胞毒性环月桂烷型倍半萜（-）-月桂联苯的全合成中的应用来说明。
The enantioselective intramolecular addition of silyl enol ethers and silyl ketene aminals onto alkyne is described. The reaction employs DTBMSegphos-Pd(II) or Binaphane-Pd(II) complexes as catalysts for the formation of methylene cyclopentane adducts from 1,6-enyne precursors. The utility of this reaction is illustrated by its application to the total synthesis of the cytotoxic cyclolaurane-type sesquiterpene, (-)-laurebiphenyl.