Design and synthesis of chiral N-chloroimidodicarbonates: application to asymmetric chlorination of silyl enol ethers.
Design and synthesis of chiral N-chloroimidodicarbonates: application to asymmetric chlorination of silyl enol ethers.
复制标题
手性N-氯亚胺二碳酸酯的设计与合成：在硅烯醇醚不对称氯化中的应用。
DOI：
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发表时间：
2007
影响因子：
3.6
通讯作者：
Debarshi Sinha
中科院分区：
文献类型：
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作者：
Saumen Hajra;Manishabrata Bhowmick;B. Maji;Debarshi Sinha
设计并合成了新型手性N-氯亚胺二碳酸酯类手性氯化试剂。其中，C(2)对称的(1R，2S，5R)-(-)-menthyl-N-chloroimidodicarbonate 2a对硅烯醇醚的氯化反应提供了中等到良好的对映体选择性(高达40%)，仅在合适的路易斯酸如Sm(OTf)(3)存在下才能生成α-氯酮。
New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C(2)-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the presence of a suitable Lewis acid such as Sm(OTf)(3).