Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes
Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes
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DOI：
10.1002/anie.200802313
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Falck, John R.
中科院分区：
文献类型：
--
作者：
He, Anyu;Falck, John R.
本文报道了α-（羟烷基）-三正丁基锡烷1的催化不对称合成，产率高，对映选择性高（e.e.达98%）。通过将乙基（三正丁基甲锡烷基）锌加成到醛中实现。在实践中，1在保护后作为其更稳定的酯或硫代氨基甲酸酯（PG）被分离。该试剂由等摩尔量的三正丁基甲锡烷基氢化物和Et 2 Zn在DME中制备，以避免抑制对映选择性的锂和镁离子的污染。
A catalytically asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes 1 in good-excellent yields and enantioselectivities (up to 98% e.e.) via addition of ethyl(tri-n-butylstannyl)zinc to aldehydes was achieved. In practice, 1 was isolated after protection as its more stable ester or thiocarbamate (PG). The reagent was prepared from equimolar amounts of tri-n-butylstannyl hydride and Et2Zn in DME so as to avoid contamination by lithium and magnesium ions which suppress enantioselectivity.