Literature DB >> 15844892

Catalytic asymmetric synthesis of hydroxy enol ethers: approach to a two-carbon homologation of aldehydes.

Sang-Jin Jeon1, Young K Chen, Patrick J Walsh.   

Abstract

[reaction: see text] Hydroboration of ethoxy acetylene, transmetalation to zinc, and addition to aldehydes in the presence of a chiral amino alcohol ligand (MIB) affords hydroxy enol ethers with high ee. The resultant enantiomerically enriched hydroxy enol ethers were converted to protected hydroxy aldehydes, a useful synthetic building block for the construction of a variety of polyoxygenated natural products. In addition, diastereoselective formation of syn- and anti-1,3-diols was studied.

Entities:  

Year:  2005        PMID： 15844892     DOI： 10.1021/ol050255n

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


  12 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

2.  Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.

Authors:  Gretchen R Stanton; Meara C Kauffman; Patrick J Walsh
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

Review 3.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Overriding Felkin control: a general method for highly diastereoselective chelation-controlled additions to alpha-silyloxy aldehydes.

Authors:  Gretchen R Stanton; Corinne N Johnson; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

5.  Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level.

Authors:  Fumitoshi Shibahara; Michael J Krische
Journal:  Chem Lett       Date:  2008       Impact factor: 1.389

Review 6.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency.

Authors:  Soo Bong Han; In Su Kim; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2009-10-16       Impact factor: 6.222

7.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

8.  Highly diastereoselective chelation-controlled additions to α-silyloxy ketones.

Authors:  Gretchen R Stanton; Gamze Koz; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-05-02       Impact factor: 15.419

9.  Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

10.  One-pot catalytic enantio- and diastereoselective syntheses of anti-, syn-cis-disubstituted, and syn-vinyl cyclopropyl alcohols.

Authors:  Hun Young Kim; Luca Salvi; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419
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