Stereoselective Synthesis of syn-β-Amino Propargylic Ethers: Application to the Asymmetric Syntheses of (+)-β-Conhydrine and (-)-Balanol
Stereoselective Synthesis of syn-β-Amino Propargylic Ethers: Application to the Asymmetric Syntheses of (+)-β-Conhydrine and (-)-Balanol
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DOI：
10.1002/adsc.201100333
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发表时间：
2011-08-01
影响因子：
5.4
通讯作者：
Voituriez, Arnaud
中科院分区：
文献类型：
--
作者：
Louvel, Julien;Chemla, Fabrice;Voituriez, Arnaud
报道了外消旋3-（甲氧基甲氧基）丙二烯基铜酸锂，特别是（氰基）和（异亚丙基）铜酸锂与对映体纯的手性N-叔丁基亚磺酰亚胺的加成反应，立体选择性合成顺式-β-氨基炔丙基醚。反应的范围和限制进行了研究。合成具有顺式-1，2-氨基醇单元的化合物的方法学的有用性通过（+）-β-conhydrine和（-）-balanol的高级中间体的不对称合成的发展而显示。
The stereoselective synthesis of syn-beta-amino propargylic ethers by the addition of racemic lithio 3-(methoxymethoxy)allenylcuprates, and more particularly (cyano) and (mesityl)cuprates, to enantiopure chiral N-tert-butylsulfinylimines is reported. The scope and limitations of the reaction is studied. The usefulness of the methodology for the synthesis of compounds having a syn-1,2-amino alcohol unit is shown through the development of the asymmetric syntheses of (+)-beta-conhydrine and of an advanced intermediate of (-)-balanol.