Literature DB >> 19161319

Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates.

Stephen N Greszler1, Jeffrey S Johnson.   

Abstract

Lanthanide triisopropoxides catalyze a rapid, tandem MPV reduction/Brook rearrangement/aldol sequence between silyl glyoxylates and aldehydes that achieves catalytic turnover through alkoxide transfer from a strain-release Lewis acidic silacycle.

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Year:  2009        PMID： 19161319      PMCID： PMC2651742          DOI： 10.1021/ol802828d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  First Catalytic Asymmetric Aldol-Tishchenko Reaction-Insight into the Catalyst Structure and Reaction Mechanism J.P.M. gratefully acknowledges receipt of an NSF Career Award (CHE-9875488), a David and Lucile Packard Fellowship and a DuPont Young Professor Grant. Support from Amoco Chemicals is also appreciated. The authors thank Prof. Joseph Templeton for helpful discussions and Andrew Larsen of the Gagné research group for assistance with vapor pressure osmometry experiments.

Authors:  Cheryl M. Mascarenhas; Steven P. Miller; Peter S. White; James P. Morken
Journal:  Angew Chem Int Ed Engl       Date:  2001-02-02       Impact factor: 15.336

2.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

3.  Tandem aldol-allylation and aldol-aldol reactions with ketone-derived enolsilanes: highly diastereoselective single-step synthesis of complex tertiary carbinols.

Authors:  Xiaolun Wang; Qinglin Meng; Nicholas R Perl; Yue Xu; James L Leighton
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

4.  Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes.

Authors:  E J Campbell; H Zhou; S T Nguyen
Journal:  Org Lett       Date:  2001-07-26       Impact factor: 6.005

5.  Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions.

Authors:  Jingjun Yin; Mark A Huffman; Karen M Conrad; Joseph D Armstrong
Journal:  J Org Chem       Date:  2006-01-20       Impact factor: 4.354

6.  Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.

Authors:  David A Nicewicz; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

7.  A reaction for sp(3)-sp(3) C-C bond formation via cooperation of Lewis acid-promoted/Rh-catalyzed C-H bond activation.

Authors:  Lei Shi; Yong-Qiang Tu; Min Wang; Fu-Min Zhang; Chun-An Fan; Yu-Ming Zhao; Wu-Jiong Xia
Journal:  J Am Chem Soc       Date:  2005-08-10       Impact factor: 15.419

8.  Synthesis and use of alpha-silyl-substituted alpha-hydroxyacetic acids.

Authors:  Carsten Bolm; Andrey Kasyan; Peter Heider; Sandra Saladin; Karlheinz Drauz; Kurt Günther; Christoph Wagner
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

9.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  Oxidation of carbon-silicon bonds: the dramatic advantage of strained siletanes.

Authors:  James D Sunderhaus; Hubert Lam; Gregory B Dudley
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  7 in total

1.  Catalytic nucleophilic glyoxylation of aldehydes.

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

2.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

3.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

4.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

5.  Direct synthesis and applications of solid silylzinc reagents.

Authors:  Revathi Chandrasekaran; Feba Thomas Pulikkottil; Krishna Suresh Elama; Ramesh Rasappan
Journal:  Chem Sci       Date:  2021-11-30       Impact factor: 9.825

6.  Alternaric acid: formal synthesis and related studies.

Authors:  Michael C Slade; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2013-01-24       Impact factor: 2.883

7.  Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.

Authors:  Matthew A Horwitz; Naoya Tanaka; Takuya Yokosaka; Daisuke Uraguchi; Jeffrey S Johnson; Takashi Ooi
Journal:  Chem Sci       Date:  2015-07-30       Impact factor: 9.825
  7 in total

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