Literature DB >> 30779574

Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives.

Bo Qu1, Renchang Tan1, Madison R Herling2, Nizar Haddad1, Nelu Grinberg1, Marisa C Kozlowski2, Xumu Zhang3, Chris H Senanayake1.   

Abstract

Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.

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Year:  2019        PMID： 30779574      PMCID： PMC6474792          DOI： 10.1021/acs.joc.8b02813

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  27 in total

1.  Synthesis and application of a new bisphosphite ligand collection for asymmetric hydroformylation of allyl cyanide.

Authors:  Christopher J Cobley; Kelli Gardner; Jerzy Klosin; Céline Praquin; Catherine Hill; Gregory T Whiteker; Antonio Zanotti-Gerosa; Jeffrey L Petersen; Khalil A Abboud
Journal:  J Org Chem       Date:  2004-06-11       Impact factor: 4.354

2.  A hybrid phosphorus ligand for highly enantioselective asymmetric hydroformylation.

Authors:  Yongjun Yan; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

3.  Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

Authors:  Thomas P Clark; Clark R Landis; Susan L Freed; Jerzy Klosin; Khalil A Abboud
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

4.  Applied hydroformylation.

Authors:  Robert Franke; Detlef Selent; Armin Börner
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

5.  Vinylation of aryl bromides using an inexpensive vinylpolysiloxane.

Authors:  Scott E Denmark; Christopher R Butler
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

6.  Origin of pressure effects on regioselectivity and enantioselectivity in the rhodium-catalyzed hydroformylation of styrene with (S,S,S)-BisDiazaphos.

Authors:  Avery L Watkins; Clark R Landis
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

7.  On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.

Authors:  Scott E Denmark; Nathan S Werner
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

Review 8.  Ligands for practical rhodium-catalyzed asymmetric hydroformylation.

Authors:  Jerzy Klosin; Clark R Landis
Journal:  Acc Chem Res       Date:  2007-11-13       Impact factor: 22.384

9.  Novel, tunable, and efficient chiral bisdihydrobenzooxaphosphole ligands for asymmetric hydrogenation.

Authors:  Wenjun Tang; Bo Qu; Andrew G Capacci; Sonia Rodriguez; Xudong Wei; Nizar Haddad; Bikashandarkoil Narayanan; Shengli Ma; Nelu Grinberg; Nathan K Yee; Dhileep Krishnamurthy; Chris H Senanayake
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

10.  Preliminary evaluation of antimicrobial activity of diastereomeric cis/trans-3-aryl(heteroaryl)-3,4-dihydroisocoumarin-4-carboxylic acids.

Authors:  Milen G Bogdanov; Meglena I Kandinska; Darina B Dimitrova; Blagovesta T Gocheva; Mariana D Palamareva
Journal:  Z Naturforsch C J Biosci       Date:  2007 Jul-Aug
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