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ChemInform Abstract: Ligand Control and Asymmetric Michael Reactions of Enantioenriched Configurationally Stable N-Boc Anilino Benzylic and Allylic Organolithium Species.

✍ Scribed by Y. S. PARK; G. A. WEISENBURGER; P. BEAK

Publisher: John Wiley and Sons
Year: 2010
Weight: 41 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199808029

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✦ Synopsis

The choice of the ligand can provide control of 1,2-vs. 1,4-addition of organolithium species to α,β-unsaturated carbonyl substrates. With (-)-sparteine as ligand highly enantioenriched configurationally stable α-lithio benzylic and allylic amine derivatives in asymmetric Michael additions give products such as (III) and (X) with high enantioselectivities at both termini of the new β,γ-bond. By further reactions as demonstrated with (XII) three continuous asymmetric centers can be generated by this methodology. -(PARK, Y.

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ChemInform Abstract: Asymmetric Carbon—Carbon Bond Formation in Michael Reactions: Conjugate Addition Reactions of Configurationally Stable Benzylic and Allylic Organolithium Species.

✍ M. D. Curtis; P. Beak 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 2 views

Conjugate Addition Reactions of Configurationally Stable Benzylic and Allylic Organolithium Species. -The organolithium species generated from the amines (I) and (IV), BuLi, and (-)-sparteine react with double activated olefins and nitro olefins to provide addition products in good yields with high