Yb(OTf)3-catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals

Yb(OTf)3-catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals
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DOI:
10.1021/ol0063860
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发表时间:
2000-10-05
期刊:
影响因子:
5.2
通讯作者:
Leighton, JL
Leighton, JL
中科院分区:
化学1区
文献类型:
--
作者:
Dreher, SD;Hornberger, KR;Leighton, JL

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以丙酮化物或亚苄基缩醛保护的1,3-二醇缩酮可以由高烯丙醇和丙酮或苯甲醛通过用HgClOAc氧化衍生的半缩酮和半缩醛而有效地合成。使用催化量的Yb(OTf)(3)对于反应的成功是至关重要的,该反应被确定为可逆的。
1,3-Diol synthons, protected as acetonides or benzylidene acetals, may be synthesized efficiently from homoallylic alcohols and acetone or benzaldehyde by oxymercuration of the derived hemiketals and hemiacetals with HgClOAc. The use of catalytic amounts of Yb(OTf)(3) is crucial to the success of the reaction, which was determined to be reversible.