A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides
A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides
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DOI：
10.1002/anie.200352632
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发表时间：
2004-01-01
影响因子：
16.6
通讯作者：
Hsung, RP
中科院分区：
文献类型：
--
作者：
Rameshkumar, C;Hsung, RP
在α-位上带有手性恶唑烷酮部分和在γ-位上带有光学活性碳原子的二烯基部分的联烯进行标题反应，得到双环和三环，非对映选择性高达90%。起始丙二烯是单（P）-或-（M）-轴向手性异构体或这些异构体的混合物。在使用纯异构体的情况下，以相似的产率和非对映选择性形成相同的产物。
Allenes bearing a chiral oxazolidinone moiety at the α-position and a dienyl moiety, bearing an optically active carbon atom, at the γ-position, undergo the title reaction to give bi-and tricycles with up to 90% diastereoselectivity. The starting allenes are either single (P)-or-(M)-axially chiral isomers or mixtures of these isomers. In the cases where pure isomers are employed, the same products are formed with similar yields and diastereoselectivities.