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β-Chloroaldehydes from Trapping Zirconium Enolates Produced in Asymmetric 1,4-Additions

Author:
Wang, Jiao Yu Joseph, Palacin, Thomas, Fletcher, Stephen P.
Source:
Organic letters 2018 v.21 no.2 pp. 378-381
ISSN:
1523-7052
Subject:
Lewis bases, carbon, chemical reactions, chemical structure, enantioselectivity, organic compounds, zirconium
Abstract:
Zirconium enolates, derived from copper-catalyzed asymmetric conjugate additions, are trapped with the Vilsmeier–Haack reagent. Asymmetric additions generate quaternary carbon centers with high enantioselectivity (generally ∼90% ee), and the enolates are converted to unsaturated β-chloroaldehydes (41–57% yields). The reaction tolerates changes to the nucleophile, can be used to form five-, six-, or seven-membered ring products, and is scalable to 5 mmol, and the products are readily elaborated by condensation, cross coupling, and addition reactions.
Agid:
6272224