- ADDITION OF ORGANOMAGNESIUM REAGENTS TO CYANOHYDRIN-O-SILYL ETHERS: AN EFFICIENT AND FLEXIBLE SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ACYLOINS
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Acyloins are prepared in high yields via reaction between Grignard reagents and O-trimethylsilyl ethers of aldehyde cyanohydrins: the method is particularly useful for the preparation of discrete acyloins in which the substituens are unsymmetrically dispo
- Gill, Melvyn,Kiefel, Milton J.,Lally, Deborah A.
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p. 1933 - 1934
(2007/10/02)
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- Tandem Alkylation-Reduction. Highly Stereoselective Synthesis of (E)-1-Hydroxymethyl Methyl Propenyl Ethers from Aldehydes Using 1-Lithio-1-methoxyallene
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Tandem alkylation-reduction of a series of aldehydes, by alkylating with 1-lithio-1-methoxyallene followed by reducing with lithium-ammonia, regiospecifically and highly stereoselectively affords the 1-hydroxymethyl methyl propenyl ether in which the alkene geometry is exclusively E.Aldehydes that have been subjected to this convenient procedure include aromatic, aliphatic, and heterocyclic aldehydes.Subsequent hydrolysis, in the aromatic and aliphatic cases, affords the corresponding α-hydroxy ethyl ketones.The stereochemistry of the propenyl ethers was established by 13C NMR spectroscopy.A mechanism for the selective reduction of the methoxyallene system is proposed.
- Weiberth, Franz J.,Hall, Stan S.
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p. 5308 - 5314
(2007/10/02)
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