Literature DB >> 12643701

Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Karen M Miller1, Wei-Sheng Huang, Timothy F Jamison.   

Abstract

A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective alpha-hydroxy ketone synthesis.

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Year:  2003        PMID： 12643701     DOI： 10.1021/ja034366y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  43 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.  Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors:  Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal:  Chemistry       Date:  2011-09-27       Impact factor: 5.236

3.  Diastereoselective Nickel-Catalyzed Reductive Couplings of Aminoaldehydes and Alkynylsilanes: Application to the Synthesis of D-erythro-Sphingosine.

Authors:  Kanicha Sa-Ei; John Montgomery
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

4.  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

5.  A surprising mechanistic "switch" in Lewis acid activation: a bifunctional, asymmetric approach to alpha-hydroxy acid derivatives.

Authors:  Ciby J Abraham; Daniel H Paull; Tefsit Bekele; Michael T Scerba; Travis Dudding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2008-12-17       Impact factor: 15.419

Review 6.  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

7.  Nickel Catalysis: Synergy between Method Development and Total Synthesis.

Authors:  Eric A Standley; Sarah Z Tasker; Kim L Jensen; Timothy F Jamison
Journal:  Acc Chem Res       Date:  2015-04-23       Impact factor: 22.384

8.  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

9.  Total synthesis of (+)-acutiphycin.

Authors:  Ryan M Moslin; Timothy F Jamison
Journal:  J Org Chem       Date:  2007-11-07       Impact factor: 4.354

10.  Stereoisomerically pure trisubstituted vinylaluminum reagents and their utility in copper-catalyzed enantioselective synthesis of 1,4-dienes containing Z or E alkenes.

Authors:  Katsuhiro Akiyama; Fang Gao; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336
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