Room temperature intramolecular hydro-O-alkylation of aldehydes:: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization

Room temperature intramolecular hydro-O-alkylation of aldehydes:: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization
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DOI:
10.1021/ol0522283
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发表时间:
2005-11-24
期刊:
影响因子:
5.2
通讯作者:
Sames, D
Sames, D
中科院分区:
化学1区
文献类型:
--
作者:
Pastine, SJ;Sames, D

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The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp(3) C-H bonds into C-O bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.