Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes

Scott E. Denmark; Tommy Bui

doi:10.1021/jo0517500

Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes

Scott E. Denmark, Tommy Bui

Chemistry

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

Abstract

Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an α-hydroxy lactone with good selectivity in a singlepot operation.

Original language	English (US)
Pages (from-to)	10190-10193
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	24
DOIs	https://doi.org/10.1021/jo0517500
State	Published - Nov 25 2005

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Organic Chemistry

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10.1021/jo0517500

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abstract = "Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an α-hydroxy lactone with good selectivity in a singlepot operation.",

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AU - Bui, Tommy

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N2 - Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an α-hydroxy lactone with good selectivity in a singlepot operation.

AB - Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an α-hydroxy lactone with good selectivity in a singlepot operation.

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Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes

Abstract

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