4.6 Article

Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylatest

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 11, 期 46, 页码 8065-8072

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41592a

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An exceptionally stereoselective and general synthesis of (Z)-alpha-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from alpha-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol condensation. Besides being an expedient synthetic procedure, the ready availability of diverse a-haloacetates, exceptional stereoselectivity, and high yields make the process a versatile transformation in organic synthesis. The potential of this method in up-scaling operations has been illustrated.

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