Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides.
作者： Ken S. Feldman , Andrew G. Karatjas
DOI: 10.1021/OL0617244
关键词: Silyl enol ether 、 Chemistry 、 Enantioselective synthesis 、 Chirality (chemistry) 、 Indole test 、 Asymmetric induction 、 Stereochemistry 、 Pummerer rearrangement 、 Chiral ligand 、 Ion pairs
摘要: The conversion of (Ss)-3-(omega-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines then oxindoles proceeds, in favorable cases, with moderate levels chirality transfer from sulfur C3 the indole core. A mechanistic model, which features either an Sn2'-like additive Pummerer sequence or a tight ion pair generated by Sn1-like vinylogous transform, is proposed rationalize sense asymmetric induction.
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