光学活性ブテノリドへの分岐アクセス:Rh/シンコナイン触媒によるタンデムC-H活性化およびマイケル付加
Dattatraya H Dethe1, Arsheed Ahmad Bhat1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India.
Abstract:
We report a highly enantioselective and efficient synthesis of C-3 substituted butenolides via a tandem C-H activation/Michael addition cascade, enabled by Rh/cinchonine dual catalysis. This strategy leverages the stability and accessibility of the achiral [Cp*RhCl2]2 complex in combination with the chiral induction provided by the naturally occurring alkaloid cinchonine, eliminating the need for complex chiral ligands. Importantly, this dual catalytic system represents the first enantioselective protocol that exploits simple acrylic acids as coupling partners, thereby extending the reactivity paradigm beyond conventional benzoic acid derivatives and significantly broadening the substrate scope beyond aromatic counterparts. The reaction proceeds in a one-pot fashion under mild conditions, delivering a wide range of products with good to very good enantiomeric excess.
関連する概念動画
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