Literature DB >> 11442401

Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from omega-alkynals via intramolecular 1-alkenylzinc/aldehyde additions.

W Oppolzer1, R N Radinov, E El-Sayed.   

Abstract

The omega-alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot reaction sequence involving alkyne monohydroboration, boron to zinc transmetalation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring closure to the aldehyde function. A general study of this macrocyclization methodology is presented with respect to ligand type, size, and nature of the formed rings.

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Year:  2001        PMID： 11442401     DOI： 10.1021/jo000463n

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


  15 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

3.  New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings.

Authors:  Mani Raj Chaulagain; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2007-07-12       Impact factor: 15.419

Review 4.  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

5.  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

6.  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 7.  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

8.  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

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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