A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis

William Chung; Petra Lindovska; Jason E. Camp

doi:10.1016/j.tetlet.2011.10.035

A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis

William Chung, Petra Lindovska, Jason E. Camp

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of α-formyl- α-allylacetates from allylic alcohols and activated alkynes has been developed. The product α-formyl-α-allylacetates were further reacted in situ to give either protected enol ethers or β-hydroxy-4-pentenoates.

Original language	English
Pages (from-to)	6785-6787
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	50
Early online date	14 Oct 2011
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.035
Publication status	Published - 14 Dec 2011
Externally published	Yes

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10.1016/j.tetlet.2011.10.035

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abstract = "A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of α-formyl- α-allylacetates from allylic alcohols and activated alkynes has been developed. The product α-formyl-α-allylacetates were further reacted in situ to give either protected enol ethers or β-hydroxy-4-pentenoates.",

keywords = "Claisen-rearrangement, DABCO, Nucleophilic catalysis, One-pot, Step-economical",

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AU - Chung, William

AU - Lindovska, Petra

AU - Camp, Jason E.

PY - 2011/12/14

Y1 - 2011/12/14

N2 - A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of α-formyl- α-allylacetates from allylic alcohols and activated alkynes has been developed. The product α-formyl-α-allylacetates were further reacted in situ to give either protected enol ethers or β-hydroxy-4-pentenoates.

AB - A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of α-formyl- α-allylacetates from allylic alcohols and activated alkynes has been developed. The product α-formyl-α-allylacetates were further reacted in situ to give either protected enol ethers or β-hydroxy-4-pentenoates.

KW - Claisen-rearrangement

KW - DABCO

KW - Nucleophilic catalysis

KW - One-pot

KW - Step-economical

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U2 - 10.1016/j.tetlet.2011.10.035

DO - 10.1016/j.tetlet.2011.10.035

M3 - Article

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VL - 52

SP - 6785

EP - 6787

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -

A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis

Abstract

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