A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.

A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.
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DOI:
10.1021/ol501715r
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发表时间:
2014-09-05
期刊:
影响因子:
5.2
通讯作者:
Pettus TR
Pettus TR
中科院分区:
化学1区
文献类型:
--
作者:
David JG;Bai WJ;Weaver MG;Pettus TR

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研究了n1 -芳基化/ c2 - o -硅基化/ c3 -甲基化和溴化/ c4 - o -甲基化吡咯与各种醛的催化非对映选择性醛醇反应。Syn加合物是由相邻的氮和氧杂原子取代基产生的。n1 -芳基残基进行氧化裂解,c3 -溴原子进行钯介导的偶联反应,两者都不会干扰新形成的立体中心。
A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3-bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters.
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