Literature DB >> 11082003

Highly regioselective and stereoselective allylation of aldehydes via palladium-catalyzed in situ hydrostannylation of allenes.

H M Chang1, C H Cheng.   

Abstract

[reaction: see text] Highly regio- and stereoselective allylation of aldehydes by allenes proceeds smoothly in aqueous/organic media in the presence of PdCl(2)(PPh(3))(2), HCl, and SnCl(2). The reaction likely occurs via hydrostannylation of allenes and allylation of aldehydes by the in situ generated allyltrichlorotins to afford the final products.

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Year:  2000        PMID: 11082003     DOI: 10.1021/ol0064563

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


  5 in total

1.  Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization.

Authors:  Michael R Luzung; Chad A Lewis; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Enantioselective carbonyl reverse prenylation from the alcohol or aldehyde oxidation level employing 1,1-dimethylallene as the prenyl donor.

Authors:  Soo Bong Han; In Su Kim; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

Review 3.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

4.  Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation.

Authors:  Khoa D Nguyen; Daniel Herkommer; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-15       Impact factor: 15.419

Review 5.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020

  5 in total

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