ChemInform Abstract: An Improved Two-Step Synthetic Route to Primary Allylic Alcohols from...
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ChemInform 2010, 41, issue 30 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de C-C bond formation O 0282 DOI: 10.1002/chin.201030042 An Improved Two-Step Synthetic Route to Primary Allylic Alcohols from Alde- hydes. — Aliphatic and aromatic aldehydes, and aldehydes bearing oxygen-containing groups adjacent to the carbonyl group undergo with triethylphosphonacetate a modified Horner—Wadsworth—Emmons reaction in a 1:1 mixture of isopropanol/water to give the corresponding α,β-unsaturated esters exclusively or predominantly as (E)-isomers. The following reduction to the alcohols is performed with AlH 3 , prepared in situ from LiAlH4 and BuBr by an improved and convenient procedure. Methoxyalane generated in situ in toluene can be also used for the 1,2-reduction of the unsaturated esters in cases where THF is not a suitable solvent. — (LIU, Z.; GONG, Y.; BYUN, H.-S.; BITTMAN*, R.; New J. Chem. 34 (2010) 3, 470-475; Dep. Chem. Biochem., Queens Coll. City Univ. N. Y., Flushing, NY 11367, USA; Eng.) — Klein 30- 042
Transcript of ChemInform Abstract: An Improved Two-Step Synthetic Route to Primary Allylic Alcohols from...
www.cheminform.wiley-vch.de
C-C bond formationO 0282 DOI: 10.1002/chin.201030042
An Improved Two-Step Synthetic Route to Primary Allylic Alcohols from Alde-hydes. — Aliphatic and aromatic aldehydes, and aldehydes bearing oxygen-containing groups adjacent to the carbonyl group undergo with triethylphosphonacetate a modified Horner—Wadsworth—Emmons reaction in a 1:1 mixture of isopropanol/water to give the corresponding α,β-unsaturated esters exclusively or predominantly as (E)-isomers. The following reduction to the alcohols is performed with AlH3, prepared in situ from LiAlH4 and BuBr by an improved and convenient procedure. Methoxyalane generated in situ in toluene can be also used for the 1,2-reduction of the unsaturated esters in cases where THF is not a suitable solvent. — (LIU, Z.; GONG, Y.; BYUN, H.-S.; BITTMAN*, R.; New J. Chem. 34 (2010) 3, 470-475; Dep. Chem. Biochem., Queens Coll. City Univ. N. Y., Flushing, NY 11367, USA; Eng.) — Klein
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ChemInform 2010, 41, issue 30 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
