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Literature DB >> 15987174

anti-1,2-Diols via Ni-catalyzed reductive coupling of alkynes and alpha-oxyaldehydes.

Torsak Luanphaisarnnont¹, Chudi O Ndubaku, Timothy F Jamison.

Abstract

[reaction: see text] Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched alpha-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes.

Entities: Chemical

Mesh：

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Year: 2005 PMID： 15987174 PMCID： PMC2522310 DOI： 10.1021/ol050881k

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

9 in total

1. Two-step synthesis of carbohydrates by selective aldol reactions.

Authors: Alan B Northrup; David W C MacMillan
Journal: Science Date: 2004-08-12 Impact factor: 47.728

2. Enantioselective organocatalytic direct aldol reactions of alpha-oxyaldehydes: step one in a two-step synthesis of carbohydrates.

Authors: Alan B Northrup; Ian K Mangion; Frank Hettche; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2004-04-13 Impact factor: 15.336

3. Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Authors:
Journal: Org Lett Date: 2000-12-28 Impact factor: 6.005

4. Diastereo- and enantioselective direct catalytic aldol reaction of 2-hydroxyacetophenones with aldehydes promoted by a heteropolymetallic complex: catalytic asymmetric synthesis of anti-1,2-diols.

Authors: Naoki Yoshikawa; Takeyuki Suzuki; Masakatsu Shibasaki
Journal: J Org Chem Date: 2002-04-19 Impact factor: 4.354

5. Anti-selective aldol reactions with titanium enolates of N-glycolyloxazolidinethiones.

Authors: Michael T Crimmins; Patrick J McDougall
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

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

Authors: Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal: J Am Chem Soc Date: 2003-03-26 Impact factor: 15.419

Review 7. Nickel-catalyzed reductive cyclizations and couplings.

Authors: John Montgomery
Journal: Angew Chem Int Ed Engl Date: 2004-07-26 Impact factor: 15.336

8. P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis.

Authors: Elizabeth A Colby; Timothy F Jamison
Journal: J Org Chem Date: 2003-01-10 Impact factor: 4.354

9. Nickel-catalyzed coupling of carbonyl compounds and alkynes or 1,3-dienes: an efficient method for the preparation of allylic, homoallylic, and bishomoallylic alcohols.

Authors: Shin-Ichi Ikeda
Journal: Angew Chem Int Ed Engl Date: 2003-11-03 Impact factor: 15.336

9 in total

14 in total

1. 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

2. 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

3. Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors: Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal: Tetrahedron Date: 2016-09-07 Impact factor: 2.457

4. Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors: Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal: European J Org Chem Date: 2010-01

5. Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

Authors: Sze-Sze Ng; Chun-Yu Ho; Timothy F Jamison
Journal: J Am Chem Soc Date: 2006-09-06 Impact factor: 15.419

6. Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors: Kanicha Sa-ei; John Montgomery
Journal: Org Lett Date: 2006-09-28 Impact factor: 6.005

7. Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

Authors: John Hartung; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2014-02-19 Impact factor: 15.336

8. Total synthesis of (+)-acutiphycin.

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

9. Origins of regioselectivity and alkene-directing effects in nickel-catalyzed reductive couplings of alkynes and aldehydes.

Authors: Peng Liu; Patrick McCarren; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal: J Am Chem Soc Date: 2010-02-17 Impact factor: 15.419

10. Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions.

Authors: P R McCarren; Peng Liu; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal: J Am Chem Soc Date: 2009-05-20 Impact factor: 15.419