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Literature DB >> 20143793

Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.

Abstract

Organozinc, -magnesium, and -lithium nucleophiles initiate a Brook/Ireland-Claisen rearrangement sequence of allylic silyl glyoxylates resulting in the formation of gamma,delta-unsaturated alpha-silyloxy acids.

Entities: Chemical Species

Mesh：

Substances：

Year: 2010 PMID： 20143793 PMCID： PMC2830285 DOI： 10.1021/ol9029353

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

8 in total

1. Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.

Authors: Stacie A Calad; K A Woerpel
Journal: J Am Chem Soc Date: 2005-02-23 Impact factor: 15.419

2. Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Authors: Brett E Howard; K A Woerpel
Journal: Tetrahedron Date: 2009-09-01 Impact factor: 2.457

3. The Cu(OTf)2- and Yb(OTf)3-catalyzed Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers.

Authors: M Hiersemann; L Abraham
Journal: Org Lett Date: 2001-01-11 Impact factor: 6.005

4. 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

5. Diastereodivergent addition of allenylzincs to aryl glyoxylates.

Authors: Thomas Hameury; Jérôme Guillemont; Luc Van Hijfte; Véronique Bellosta; Janine Cossy
Journal: Org Lett Date: 2009-06-04 Impact factor: 6.005

6. Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.

Authors: Brett E Howard; K A Woerpel
Journal: Org Lett Date: 2007-10-02 Impact factor: 6.005

7. Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

Authors: Stephen N Greszler; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. Catalytic diastereoselective reductive claisen rearrangement.

Authors: Steven P Miller; James P Morken
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

8 in total

11 in total

1. 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

2. Catalytic nucleophilic glyoxylation of aldehydes.

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

3. Three-component coupling approach to trachyspic acid.

Authors: Daniel C Schmitt; Leighann Lam; Jeffrey S Johnson
Journal: Org Lett Date: 2011-08-31 Impact factor: 6.005

4. Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.

Authors: Daniel C Schmitt; Ericka J Malow; Jeffrey S Johnson
Journal: J Org Chem Date: 2012-03-15 Impact factor: 4.354

5. Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Authors: Stephanie A Murray; Michael Z Liang; Simon J Meek
Journal: J Am Chem Soc Date: 2017-09-27 Impact factor: 15.419

6. Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.

Authors: Gregory R Boyce; Shubin Liu; Jeffrey S Johnson
Journal: Org Lett Date: 2012-01-11 Impact factor: 6.005

7. 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

8. 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

9. 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

10. An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.

Authors: Gregory R Boyce; Jeffrey S Johnson
Journal: J Org Chem Date: 2016-02-02 Impact factor: 4.354