- An expedient synthesis of olfactory lactones by intramolecular hydroacylalkoxylation reactions
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A series of 4,5-disubstituted γ-lactones, including whisky and cognac lactones, was synthesised in four steps from a readily available chiral precursor. By using an intramolecular hydroacylalkoxylation reaction in the final step, a correlation between the (E)/(Z) configuration of the precursor and the product distribution has been established, for the first time, in this type of cyclisation reactions. Copyright
- Adrio, Luis A.,Hii, King Kuok Mimi
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p. 1852 - 1857
(2011/05/05)
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- Solid-support synthesis of 1,2-diols and γ-lactones through addition of α-(benzoyloxy)crotylindium reagents to aldehydes
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A procedure for the solid phase synthesis of 1,2-diols and γ-lactones from α-(hydroxy)crotylstannane has been developed through transmetalation with InBr3. A variety of 1,2-diols and γ-lactones were synthesized in satisfactory yields and, in some cases, with excellent diastereoselectivity. The products are formed free of tin contamination.
- Cossy, Janine,Rasamison, Chrystelle,Pardo, Domingo Gomez,Marshall, James A.
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p. 629 - 633
(2007/10/03)
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- Stereoselective Thermal Reactions between (E)-1-Alkoxymethoxybut-2-enyl(tributyl)stannanes and Aldehydes
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(E)-1-Methoxymethoxybut-2-enyl(tributyl)stannane (6), readily available by the addition of tributylstannyl-lithium to crotonaldehyde and alkylation of the adduct using chloromethyl methyl ether, reacts on heating with aldehydes to give anti-4-hydroxy-3-methyl-cis-1,2-enol ethers.These on hydrolysis and oxidation provide trans-4,5-disubstituted butyrolactones.
- Pratt, Andrew J.,Thomas, Eric J.
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p. 1521 - 1527
(2007/10/02)
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- On The Use of E-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-Selective, Homo-enolate Equivalent
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(E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyl-lithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4-hydroxy-3-methyl-cis-1,2-enol ethers, hydrolysis and oxidation of which provides a stereoselective route to trans-4,5-disubstituted butyrolactones.
- Pratt, Andrew J.,Thomas, Eric J.
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p. 1115 - 1117
(2007/10/02)
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