Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral α-Branched Amines
Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral α-Branched Amines
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DOI：
10.1021/jo902424m
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发表时间：
2010-02-05
影响因子：
3.6
通讯作者：
Lin, Guo-Qiang
中科院分区：
文献类型：
--
作者：
Chen, Bai-Ling;Wang, Bing;Lin, Guo-Qiang
氯化炔基镁与 N-叔丁亚磺酰亚胺的加成反应具有非常高的非对映选择性（dr > 13:1，大部分是非对映纯），并且具有两种反应伙伴的一般范围。高 Dr 转化为简化的纯化和更高的光学纯度，用于合成各种手性 α 支化胺。炔烃官能团还为进一步的合成转化提供了多种机会。利用该方法实现了 (+)-angustureine 7 和 (-)-cuspareine 10 的简短不对称合成。
The addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl imines proceeded with a remarkably high diastereoselectivity (dr > 13:1, mostly diastereopure), and with a general scope of both reaction partners. The high dr translated into simplified purification and higher optical purity for the synthesis of a wide array of chiral alpha-branched amines. The alkyne functionality also provides a multitude of opportunities for further synthetic transformations. The short asymmetric synthesis of (+)-angustureine 7 and (-)-cuspareine 10 was realized with use of this approach.