ChemInform Abstract: Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl...

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1999 alcohols alcohols (benzene compounds) Q 0230 24 - 083 Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2- Heteroaryl-allyl Alcohols. — Lithiation of compounds (I), (V) and (VIII) generates α-substituted masked alkenyllithiums which react with carbonyl com- pounds to provide allylic silyl ethers via a [1,4]-C → O silicon rearrangement. Following deprotection provides the corresponding alcohols. In the case of (VIII), the intermediate silyl ether is unstable and directly hydrolyzed during chromatography. — (KATRITZKY, ALAN R.; TOADER, DORIN; WANG, XIAOJING; J. Org. Chem. 63 (1998) 26, 9978-9982; Cent. Heterocycl. Comp., Dep. Chem., Univ. Fla., Gainesville, FL 32611, USA; EN) 1

Transcript of ChemInform Abstract: Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl...

Page 1: ChemInform Abstract: Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols.

1999 alcohols

alcohols (benzene compounds)Q 0230

24 - 083Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols. — Lithiation of compounds (I), (V) and (VIII)generates α-substituted masked alkenyllithiums which react with carbonyl com-pounds to provide allylic silyl ethers via a [1,4]-C → O silicon rearrangement.Following deprotection provides the corresponding alcohols. In the case of(VIII), the intermediate silyl ether is unstable and directly hydrolyzed duringchromatography. — (KATRITZKY, ALAN R.; TOADER, DORIN; WANG,XIAOJING; J. Org. Chem. 63 (1998) 26, 9978-9982; Cent. Heterocycl. Comp.,Dep. Chem., Univ. Fla., Gainesville, FL 32611, USA; EN)

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