Absolute configuration of 2-(tributylstannyl)pyrrolidine by anomalous dispersion X-ray analysis

Absolute configuration of 2-(tributylstannyl)pyrrolidine by anomalous dispersion X-ray analysis
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DOI:
10.1021/jo048569w
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发表时间:
2005-01-07
影响因子:
3.6
通讯作者:
Vicic, DA
Vicic, DA
中科院分区:
化学2区
文献类型:
--
作者:
Gawley, RE;Narayan, S;Vicic, DA

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对映纯的2-(三丁基锡烷基)吡咯烷氢碘酸盐可以通过相应的N-Boc化合物的TMSI处理以优异的产率制备,N-Boc化合物又通过不对称去质子化(s-BuLi(.)金雀花碱)和甲锡烷基化。获得了适合于X射线分析的氢碘酸盐晶体,尽管丁基存在一些无序,但使用反常色散的分析确定了绝对构型为S。
Enantiopure 2-(tributylstannyl)pyrrolidine hydroiodide may be prepared in excellent yield by TMSI treatment of the corresponding N-Boc compound, which is in turn prepared by asymmetric deprotonation (s-BuLi(.)sparteine) and stannylation, as described in the literature. Crystals of the hydroiodide salt suitable for X-ray analysis were obtained, and although there is some disorder about the butyl groups, analysis using anomalous dispersion establishes the absolute configuration as S.