Highly diastereoselective addition of silyl enolates to chiral imines derived from (S)-valine methyl ester using lanthanide triflate.

Highly diastereoselective addition of silyl enolates to chiral imines derived from (S)-valine methyl ester using lanthanide triflate.
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DOI:
10.1016/0040-4039(96)00108-6
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发表时间:
1996-03-04
影响因子:
1.8
通讯作者:
UmaniRonchi, A
UmaniRonchi, A
中科院分区:
化学4区
文献类型:
--
作者:
Cozzi, PG;DiSimone, B;UmaniRonchi, A

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以Yb(OTf)(3)为催化剂,在室温下,以乙醛、手性胺和硅烯酸酯为原料,一锅法合成了β-氨基酸酯、β-氨基酸前体和β-内酰胺类抗生素。通过使用(S)-缬氨酸甲酯作为手性胺,实现了优良到良好水平的非对映选择性。
One-pot highly diastereoselective synthesis of beta-amino esters, precursors of beta-amino acids and beta-lactam antibiotics has been accomplished starting from an aldehyde, a chiral amine and a silyl enolate using Yb(OTf)(3) as a catalyst at room temperature. Excellent to good levels of diastereoselection have been achieved by the use of (S)-Valine methyl ester as chiral amine.