The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst

Guang Hui Deng; Hui Hu; Han Xun Wei; Paul W. Paré

doi:10.1002/hlca.200390294

The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI₂) as Catalyst

Guang Hui Deng, Hui Hu, Han Xun Wei, Paul W. Paré

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23 Scopus citations

Abstract

Stereoselective synthesis of (Z)-α-(hydroxyalkyl)-β -iodoacrylates (=(2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me₃SiI, and an alkanal under mild conditions with MgI₂ as catalyst (→ 1-9; see Table and Scheme 1). Baylis-Hillman β-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

Original language	English
Pages (from-to)	3510-3515
Number of pages	6
Journal	Helvetica Chimica Acta
Volume	86
Issue number	10
DOIs	https://doi.org/10.1002/hlca.200390294
State	Published - 2003

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title = "The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst",

abstract = "Stereoselective synthesis of (Z)-α-(hydroxyalkyl)-β -iodoacrylates (=(2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (→ 1-9; see Table and Scheme 1). Baylis-Hillman β-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).",

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T1 - The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst

AU - Deng, Guang Hui

AU - Hu, Hui

AU - Wei, Han Xun

AU - Paré, Paul W.

PY - 2003

Y1 - 2003

N2 - Stereoselective synthesis of (Z)-α-(hydroxyalkyl)-β -iodoacrylates (=(2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (→ 1-9; see Table and Scheme 1). Baylis-Hillman β-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

AB - Stereoselective synthesis of (Z)-α-(hydroxyalkyl)-β -iodoacrylates (=(2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (→ 1-9; see Table and Scheme 1). Baylis-Hillman β-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

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The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst

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The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI₂) as Catalyst