Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.
Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.
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DOI：
10.1021/ja1072614
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发表时间：
2010-10-13
影响因子：
15
通讯作者：
Zhang L
中科院分区：
文献类型：
--
作者：
Lu B;Li C;Zhang L
以8-烷基喹啉N-氧化物为氧化剂，在无酸添加剂的条件下，金催化的内炔分子间氧化反应具有高的区域选择性。以良好至优异的产率和优异的E-选择性获得合成通用的α，β-不饱和羰基。容许一系列官能团，例如THP、莫莫、N3、OTBS和N-Boc。该反应允许将α，β-不饱和羰基掩蔽为炔丙基部分，从而为在复杂结构的合成中可能遇到的官能团与α，β-不饱和羰基的相容性问题提供了实用的解决方案。
Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylqinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N3, OTBS, and N-Boc are tolerated. This reaction allows to mask α,β-unsaturated carbonyls as propargyl moieties, thus offering a practical solution to issues of functional group compatibility with α,β-unsaturated carbonyls, likely encountered in syntheses of complex structures.
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影响因子：
5.2
作者：
Al-Rashid, Ziyad F.;Hsung, Richard P.
通讯作者：
Hsung, Richard P.
影响因子：
2.8
作者：
SUN, SH;EDWARDS, JO;CURCI, R
通讯作者：
CURCI, R
影响因子：
2
作者：
Couty, Sylvain;Meyer, Christophe;Cossy, Janine
通讯作者：
Cossy, Janine
影响因子：
3.6
作者：
SRINIVASAN, NS;LEE, DG
通讯作者：
LEE, DG
影响因子：
3.6
作者：
Taber, DF;Herr, RJ;Geremia, JM
通讯作者：
Geremia, JM