Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals.

Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals.
复制标题

使用 Z,E-乙烯基乙烯酮 N,O-缩醛与缩醛进行顺式选择性乙烯基向山醇醛反应。

DOI:
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发表时间:
2017
期刊:
影响因子:
5.2
通讯作者:
Seijiro Hosokawa
Seijiro Hosokawa
中科院分区:
化学1区
文献类型:
--
作者:
Naoya Sagawa;Hiroki Moriya;Seijiro Hosokawa

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以(E)-3-戊烯酸和l-缬氨酸为原料,合成了具有手性助剂的Z,E-乙烯基烯酮甲硅烷基N,O-缩醛,实现了乙烯基-Mukaiyama羟醛缩合反应的立体选择性。反应顺利进行,得到高立体选择性的顺式加成物。由于产物具有δ-烷氧基-γ-甲基-α,β-不饱和酰亚胺结构,该反应适合于短流程合成聚酮化合物。
Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and l-valine, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.
DOI: 10.1021/ja027638q
发表时间: 2003-09-10
影响因子: 15
作者:
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通讯作者: Connell, BT
DOI: 10.1002/anie.201308264
发表时间: 2014-01-03
影响因子: 16.6
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