Literature DB >> 19191696

Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

Barry M Trost1, Sushant Malhotra, Benjamin A Fried.   

Abstract

Magnesium-catalyzed enantioselective aldol between ethyl diazoacetate and aromatic, aliphatic, and alpha,beta-unsaturated aldehydes affords alpha-diazo-beta-hydroxy-esters in high enantioselectivities. Aldol adducts resulting from this asymmetric transformation are versatile intermediates toward the synthesis of several ester containing chiral building blocks.

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Year:  2009        PMID： 19191696      PMCID： PMC2652472          DOI： 10.1021/ja809181m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

Authors:  Wengang Yao; Jianbo Wang
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

2.  The first direct and enantioselective cross-aldol reaction of aldehydes.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

3.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction.

Authors:  Barry M Trost; Alec Fettes; Brock T Shireman
Journal:  J Am Chem Soc       Date:  2004-03-10       Impact factor: 15.419

4.  Highly diastereo- and enantioselective copper-catalyzed domino reduction/aldol reaction of ketones with methyl acrylate.

Authors:  Julia Deschamp; Olivier Chuzel; Jérôme Hannedouche; Olivier Riant
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-13       Impact factor: 15.336

5.  Highly anti-selective catalytic aldol reactions of amides with aldehydes.

Authors:  Susumu Saito; Shu Kobayashi
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

6.  Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates.

Authors:  David A Evans; C Wade Downey; Jed L Hubbs
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

7.  Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Authors:  Wolfgang Notz; Fujie Tanaka; Carlos F Barbas
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

8.  Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst.

Authors:  Hong Li; Chao-Shan Da; Yu-Hua Xiao; Xiao Li; Ya-Ning Su
Journal:  J Org Chem       Date:  2008-08-14       Impact factor: 4.354

9.  CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters.

Authors:  Bruce H Lipshutz; Benjamin Amorelli; John B Unger
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419

10.  Direct catalytic asymmetric aldol-Tishchenko reaction.

Authors:  Vijay Gnanadesikan; Yoshihiro Horiuchi; Takashi Ohshima; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419
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  16 in total

Review 1.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

2.  Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

Authors:  Michael T Corbett; Daisuke Uraguchi; Takashi Ooi; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

3.  Catalytic nucleophilic glyoxylation of aldehydes.

Authors:  Kimberly M Steward; Jeffrey S Johnson
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

4.  Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.

Authors:  Kimberly M Steward; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

5.  Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

Authors:  Barry M Trost; Sushant Malhotra; Philipp Koschker; Pascal Ellerbrock
Journal:  J Am Chem Soc       Date:  2012-01-18       Impact factor: 15.419

6.  Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Authors:  Yi Luan; Yue Qi; Hongyi Gao; Qianqian Ma; Scott E Schaus
Journal:  European J Org Chem       Date:  2014-11-01

7.  Total synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle; Daniel Hund
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

8.  BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.

Authors:  Anil K Gupta; Munmun Mukherjee; Gang Hu; William D Wulff
Journal:  J Org Chem       Date:  2012-09-04       Impact factor: 4.354

9.  Dinuclear zinc-ProPhenol-catalyzed enantioselective α-hydroxyacetate aldol reaction with activated ester equivalents.

Authors:  Barry M Trost; David J Michaelis; Mihai I Truica
Journal:  Org Lett       Date:  2013-08-15       Impact factor: 6.005

10.  PREPARATION OF ISOPROPYL 2-DIAZOACETYL(PHENYL)CARBAMATE.

Authors:  Hubert Muchalski; Amanda B Doody; Timothy L Troyer; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2011-02-08
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