Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: synthesis and structure elucidation of capensifuranone.
Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: synthesis and structure elucidation of capensifuranone.
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DOI：
10.1021/jo049567e
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发表时间：
2004-07
期刊：
影响因子：
--
通讯作者：
David R. Williams;A. Nold;R. Mullins
中科院分区：
文献类型：
--
作者：
David R. Williams;A. Nold;R. Mullins
卡彭西呋喃酮 (1) 的合成是通过应用有机铜试剂与非外消旋 N-烯酰基-4-苯基-1,3-恶唑烷酮的不对称共轭加成反应的进展来实现的，用于制备 1,3-syn-二甲基阵列。 1 的相对和绝对立体化学的分配是根据合成二醇衍生物的高场 NMR 表征进行的。先前未指定的 1 的 C4 立体化学被确定为 (S)-构型。已检查了卡彭西呋酮及其 C4 非对映体的热力学平衡。
The synthesis of capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arrays. The assignment of relative and absolute stereochemistry of 1 has been made following the high-field NMR characterizations of synthetic diol derivatives. The previously unassigned C4 stereochemistry of 1 was determined to be of the (S)-configuration. The thermodynamic equilibration of capensifuranone and its C4 diastereomer has been examined.