DFT investigation on Lewis base-catalyzed Lewis acid-mediated reactions: hypervalent silicon species as chiral organocatalysts in (direct) aldol reactions

Sergio Rossi; Maurizio Benaglia; Laura Maria Raimondi

doi:10.1039/d0nj03976d

DFT investigation on Lewis base-catalyzed Lewis acid-mediated reactions: hypervalent silicon species as chiral organocatalysts in (direct) aldol reactions

New Journal of Chemistry ◽

10.1039/d0nj03976d ◽

2020 ◽

Vol 44 (44) ◽

pp. 19288-19293

Author(s):

Sergio Rossi ◽

Maurizio Benaglia ◽

Laura Maria Raimondi

Keyword(s):

Lewis Acid ◽

Aldol Reaction ◽

Aromatic Aldehydes ◽

Lewis Base ◽

Aldol Reactions ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Direct Aldol Reaction

The stereoselective organocatalytic addition of silyl enol ethers to aromatic aldehydes catalyzed by bisphosphoramides and the direct aldol reaction between ketones and aromatic aldehydes promoted by phosphinoxides in the presence of tetrachlorosilane were investigated by the DFT approach.

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ChemInform Abstract: Enantioselective and Diastereoselective Catalysis of the Mukaiyama Aldol Reaction: Ene Mechanism in Titanium-Catalyzed Aldol Reactions of Silyl Enol Ethers.

ChemInform ◽

10.1002/chin.199349056 ◽

2010 ◽

Vol 24 (49) ◽

pp. no-no

Author(s):

K. MIKAMI ◽

S. MATSUKAWA

Keyword(s):

Aldol Reaction ◽

Aldol Reactions ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Mukaiyama Aldol Reaction ◽

Mukaiyama Aldol

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Asymmetric Mukaiyama aldol reaction of silyl enol ethers with aldehydes using a polymer-supported chiral Lewis acid catalyst

Tetrahedron ◽

10.1016/j.tet.2005.07.110 ◽

2005 ◽

Vol 61 (51) ◽

pp. 12074-12080 ◽

Cited By ~ 21

Author(s):

Shinichi Itsuno ◽

Shinnosuke Arima ◽

Naoki Haraguchi

Keyword(s):

Lewis Acid ◽

Aldol Reaction ◽

Acid Catalyst ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Mukaiyama Aldol Reaction ◽

Chiral Lewis Acid ◽

Mukaiyama Aldol ◽

Lewis Acid Catalyst ◽

Polymer Supported

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Asymmetric Mukaiyama Aldol Reaction of Silyl Enol Ethers with Aldehydes Using a Polymer-Supported Chiral Lewis Acid Catalyst.

ChemInform ◽

10.1002/chin.200616032 ◽

2006 ◽

Vol 37 (16) ◽

Author(s):

Shinichi Itsuno ◽

Shinnosuke Arima ◽

Naoki Haraguchi

Keyword(s):

Lewis Acid ◽

Aldol Reaction ◽

Acid Catalyst ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Mukaiyama Aldol Reaction ◽

Chiral Lewis Acid ◽

Mukaiyama Aldol ◽

Lewis Acid Catalyst ◽

Polymer Supported

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Lewis acid promoted aldol reaction of fluorinated silyl enol ethers from new fluoroacetylsilane derivatives

Tetrahedron Letters ◽

10.1016/j.tetlet.2004.05.055 ◽

2004 ◽

Vol 45 (28) ◽

pp. 5403-5406 ◽

Cited By ~ 20

Author(s):

Woo Jin Chung ◽

Silvana C. Ngo ◽

Seiichiro Higashiya ◽

John T. Welch

Keyword(s):

Lewis Acid ◽

Aldol Reaction ◽

Enol Ethers ◽

Silyl Enol Ethers

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Enantioselective and diastereoselective catalysis of the Mukaiyama aldol reaction: ene mechanism in titanium-catalyzed aldol reactions of silyl enol ethers

Journal of the American Chemical Society ◽

10.1021/ja00068a098 ◽

1993 ◽

Vol 115 (15) ◽

pp. 7039-7040 ◽

Cited By ~ 114

Author(s):

Koichi Mikami ◽

Satoru Matsukawa

Keyword(s):

Aldol Reaction ◽

Aldol Reactions ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Mukaiyama Aldol Reaction ◽

Mukaiyama Aldol

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Lewis acid catalysis in micellar systems. Sc(OTf)3-Catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant

Tetrahedron Letters ◽

10.1016/s0040-4039(97)00854-x ◽

1997 ◽

Vol 38 (26) ◽

pp. 4559-4562 ◽

Cited By ~ 110

Author(s):

Shū Kobayashi ◽

Takeshi Wakabayashi ◽

Satoshi Nagayama ◽

Hidekazu Oyamada

Keyword(s):

Lewis Acid ◽

Acid Catalysis ◽

Aldol Reactions ◽

Lewis Acid Catalysis ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Micellar Systems

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Lewis Acid Promoted Aldol Reaction of Fluorinated Silyl Enol Ethers from New Fluoroacetylsilane Derivatives.

ChemInform ◽

10.1002/chin.200442086 ◽

2004 ◽

Vol 35 (42) ◽

Author(s):

Woo Jin Chung ◽

Silvana C. Ngo ◽

Seiichiro Higashiya ◽

John T. Welch

Keyword(s):

Lewis Acid ◽

Aldol Reaction ◽

Enol Ethers ◽

Silyl Enol Ethers

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Chiral Lewis Acid Catalysis in Aqueous Media. Catalytic Asymmetric Aldol Reactions of Silyl Enol Ethers with Aldehydes in a Protic Solvent Including Water

Chemistry Letters ◽

10.1246/cl.1999.71 ◽

1999 ◽

Vol 28 (1) ◽

pp. 71-72 ◽

Cited By ~ 46

Author(s):

Shu Kobayashi ◽

Satoshi Nagayama ◽

Tsuyoshi Busujima

Keyword(s):

Lewis Acid ◽

Acid Catalysis ◽

Aqueous Media ◽

Aldol Reactions ◽

Protic Solvent ◽

Lewis Acid Catalysis ◽

Asymmetric Aldol ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Chiral Lewis Acid

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ChemInform Abstract: Chiral Lewis Acid Catalysis in Aqueous Media. Catalytic Asymmetric Aldol Reactions of Silyl Enol Ethers with Aldehydes in a Protic Solvent Including Water.

ChemInform ◽

10.1002/chin.199924029 ◽

2010 ◽

Vol 30 (24) ◽

pp. no-no

Author(s):

Shu Kobayashi ◽

Satoshi Nagayama ◽

Tsuyoshi Busujima

Keyword(s):

Lewis Acid ◽

Acid Catalysis ◽

Aqueous Media ◽

Aldol Reactions ◽

Protic Solvent ◽

Lewis Acid Catalysis ◽

Asymmetric Aldol ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Chiral Lewis Acid

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ChemInform Abstract: Lewis Acid Catalysis in Micellar Systems. Sc(OTf)3-Catalyzed Aqueous Aldol Reactions of Silyl Enol Ethers with Aldehydes in the Presence of a Surfactant.

ChemInform ◽

10.1002/chin.199740054 ◽

2010 ◽

Vol 28 (40) ◽

pp. no-no

Author(s):

S. KOBAYASHI ◽

T. WAKABAYASHI ◽

S. NAGAYAMA ◽

H. OYAMADA

Keyword(s):

Lewis Acid ◽

Acid Catalysis ◽

Aldol Reactions ◽

Lewis Acid Catalysis ◽

Enol Ethers ◽

Silyl Enol Ethers ◽

Micellar Systems

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