Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines

Gert Callebaut; Filip Colpaert; Melinda Nonn; Loránd Kiss; Reijo Sillanpää; Karl W. Törnroos; Ferenc Fülöp; Norbert De Kimpe; Sven Mangelinckx

doi:10.1039/c4ob00243a

Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines

Organic & Biomolecular Chemistry ◽

10.1039/c4ob00243a ◽

2014 ◽

Vol 12 (21) ◽

pp. 3393-3405 ◽

Cited By ~ 6

Author(s):

Gert Callebaut ◽

Filip Colpaert ◽

Melinda Nonn ◽

Loránd Kiss ◽

Reijo Sillanpää ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Stereoselective Synthesis ◽

Building Blocks

Mannich-type reactions across N-sulfinyl-α-chloroaldimines resulted in syn-stereoselective synthesis of chloroisothreonine derivatives as excellent building blocks.

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Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck−Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (−)-Indatraline

The Journal of Organic Chemistry ◽

10.1021/jo102134v ◽

2011 ◽

Vol 76 (3) ◽

pp. 857-869 ◽

Cited By ~ 55

Author(s):

Jason G. Taylor ◽

Carlos Roque D. Correia

Keyword(s):

Asymmetric Synthesis ◽

Stereoselective Synthesis ◽

Building Blocks ◽

Formal Synthesis

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ChemInform Abstract: Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-Indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal

ChemInform ◽

10.1002/chin.201119088 ◽

2011 ◽

Vol 42 (19) ◽

pp. no-no

Author(s):

Jason G. Taylor ◽

Carlos Roque D. Correia

Keyword(s):

Asymmetric Synthesis ◽

Stereoselective Synthesis ◽

Building Blocks

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Correction to Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck–Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (–)-Indatraline

The Journal of Organic Chemistry ◽

10.1021/jo300821w ◽

2012 ◽

Vol 77 (11) ◽

pp. 5220-5220 ◽

Cited By ~ 2

Author(s):

Jason G. Taylor ◽

Carlos Roque D. Correia

Keyword(s):

Asymmetric Synthesis ◽

Stereoselective Synthesis ◽

Building Blocks ◽

Formal Synthesis

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Regio- and Stereoselective Synthesis of α-Chiral 2-Substituted 4-Bromothiazoles from 2,4-Dibromothiazole by Bromine-Magnesium Exchange. Building Blocks for the Synthesis of Thiazolyl Peptides and Dolabellin

Synlett ◽

10.1055/s-2003-43361 ◽

2004 ◽

pp. 131-133 ◽

Cited By ~ 1

Author(s):

Thorsten Bach ◽

Alexandra Spieß ◽

Golo Heckmann

Keyword(s):

Stereoselective Synthesis ◽

Building Blocks ◽

Magnesium Exchange

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Enantiomerically Enriched Cyclopropene Derivatives: Versatile Building Blocks in Asymmetric Synthesis

Angewandte Chemie International Edition ◽

10.1002/anie.200890046 ◽

2008 ◽

Vol 47 (11) ◽

pp. 1982-1982 ◽

Cited By ~ 6

Author(s):

Ilan Marek ◽

Samah Simaan ◽

Ahmad Masarwa

Keyword(s):

Asymmetric Synthesis ◽

Building Blocks

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Cellulose recycling as a source of raw chirality

Pure and Applied Chemistry ◽

10.1351/pac-con-12-11-10 ◽

2013 ◽

Vol 85 (8) ◽

pp. 1683-1692 ◽

Cited By ~ 23

Author(s):

Valeria Corne ◽

María Celeste Botta ◽

Enrique D. V. Giordano ◽

Germán F. Giri ◽

David F. Llompart ◽

...

Keyword(s):

Organic Chemistry ◽

Organic Carbon ◽

Asymmetric Synthesis ◽

Building Blocks ◽

Biologically Active ◽

Raw Material ◽

Chiral Auxiliaries ◽

High Chemical ◽

Chiral Structure

Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. Biomass has been demonstrated to be a widely available raw material that represents the only abundant source of renewable organic carbon. Through the pyrolitic conversion of cellulose or cellulose-containing materials it is possible to produce levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

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8-Oxabicyclo[3.2.1]oct-6-en-3-ones: Application to the Asymmetric Synthesis of Polyoxygenated Building Blocks

ChemInform ◽

10.1002/chin.200424268 ◽

2004 ◽

Vol 35 (24) ◽

Author(s):

Ingo V. Hartung ◽

H. Martin R. Hoffmann

Keyword(s):

Asymmetric Synthesis ◽

Building Blocks

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Asymmetric synthesis of allylic sulfones useful as asymmetric building blocks.

Journal of the American Chemical Society ◽

10.1021/ja00143a007 ◽

1995 ◽

Vol 117 (38) ◽

pp. 9662-9670 ◽

Cited By ~ 91

Author(s):

Barry M. Trost ◽

Michael G. Organ ◽

George A. O'Doherty

Keyword(s):

Asymmetric Synthesis ◽

Building Blocks ◽

Asymmetric Building

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Stereoselective synthesis of chiral tertiary alcohol building blocks via neighbouring group participation from tri-substituted olefins

Tetrahedron Letters ◽

10.1016/j.tetlet.2007.12.046 ◽

2008 ◽

Vol 49 (7) ◽

pp. 1169-1174 ◽

Cited By ~ 8

Author(s):

Sadagopan Raghavan ◽

T. Sreekanth

Keyword(s):

Stereoselective Synthesis ◽

Building Blocks ◽

Tertiary Alcohol ◽

Group Participation ◽

Neighbouring Group Participation

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ChemInform Abstract: Polyalkoxy Nitrones as Chiral Building Blocks in Asymmetric Synthesis

ChemInform ◽

10.1002/chin.200013278 ◽

2010 ◽

Vol 31 (13) ◽

pp. no-no

Author(s):

Pedro Merino ◽

Tomas Tejero

Keyword(s):

Asymmetric Synthesis ◽

Building Blocks

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Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines

Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck−Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (−)-Indatraline

ChemInform Abstract: Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-Indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal

Correction to Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck–Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (–)-Indatraline

Regio- and Stereoselective Synthesis of α-Chiral 2-Substituted 4-Bromo­thiazoles from 2,4-Dibromothiazole by Bromine-Magnesium Exchange. ­Building Blocks for the Synthesis of Thiazolyl Peptides and Dolabellin

Enantiomerically Enriched Cyclopropene Derivatives: Versatile Building Blocks in Asymmetric Synthesis

Cellulose recycling as a source of raw chirality

8-Oxabicyclo[3.2.1]oct-6-en-3-ones: Application to the Asymmetric Synthesis of Polyoxygenated Building Blocks

Asymmetric synthesis of allylic sulfones useful as asymmetric building blocks.

Stereoselective synthesis of chiral tertiary alcohol building blocks via neighbouring group participation from tri-substituted olefins

ChemInform Abstract: Polyalkoxy Nitrones as Chiral Building Blocks in Asymmetric Synthesis

Regio- and Stereoselective Synthesis of α-Chiral 2-Substituted 4-Bromothiazoles from 2,4-Dibromothiazole by Bromine-Magnesium Exchange. Building Blocks for the Synthesis of Thiazolyl Peptides and Dolabellin