通过手性转移立体选择性制备 P-轴向手性烯丙基双膦氧化物。
Stereoselective preparation of P,axial-stereogenic allenyl bisphosphine oxides via chirality-transfer.
机构信息
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China.
出版信息
Org Biomol Chem. 2020 Apr 29;18(16):3017-3021. doi: 10.1039/d0ob00390e.
PMID:32236276
Abstract
P,C-Stereogenic propargyl alcohols RC-3/SC-3' were prepared by the addition of (L)-menthyl-derived SPOs to propynals, which were converted to P,axial-stereogenic allenyl bisphosphine oxides. The chirality transfer was controlled by α-carbon via syn [2,3]-sigmatropic rearrangement. For SC-3' linking weak WDG on the alkynyl moiety, the chirality on the axis depended on stereogenic phosphorus.
摘要
手性中心 P、C-丙炔醇 RC-3/SC-3' 通过（L）-薄荷衍生的 SPO 对丙炔醛加成制备，丙炔醛被转化为 P、轴向手性烯丙基双膦氧化物。手性转移通过α-碳通过顺[2,3]-σ重排控制。对于 SC-3' 将弱 WDG 连接到炔基部分，轴上的手性取决于手性磷。
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