- METHOD FOR PRODUCING LAVANDULAL
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Provided is a method of producing lavandulal at a high yield by controlling formation of its isomer of lavandulal as a by-product. In a method of producing lavandulal by making an acetal compound represented by the following formula (I) react with 3-methyl-1-butene-3-ol in the presence of an acid catalyst, the method includes: adding, to a liquid mixture comprising an acid catalyst, an acetal compound represented by the following formula (I), and 3-methyl-1-butene-3-ol in at least a portion of an amount to be used (3-methyl-1-butene-3-ol (a)), 3-methyl-1-butene-3-ol in the other portion of the amount to be used (3-methyl-1-butene-3-ol (b)); and maintaining the liquid mixture at a temperature of 110° C. or higher: in which Each R in the formula (I) represents an alkyl group.
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Paragraph 0042
(2016/04/20)
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- Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted N-Acylbornane-10,2-sultams under Mild Conditions: An Efficient Synthesis of Enantiomerically Pure Ketones and Aldehydes
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α-Substituted N-acylbornane-10,2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5, 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an -mediated coupling of the resulting S-benzyl thioesters with Grignard reagents.Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10,2-sultams 6 via a one-step reduction with (i-Bu)2AlH.No epimerization at the α-chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane-10,2-sultam 1 or ent-1, was recovered.By using this methodology, several natural products or precursors thereof can be prepared.
- Oppolzer, Wolfgang,Darcel, Christophe,Rochet, Patrick,Rosset, Stephane,Brabander, Jef De
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p. 1319 - 1337
(2007/10/03)
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