Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Literature DB >> 16986920

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

Abstract

The catalytic, diastereoselective coupling of alpha-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excellent across a range of substrates.

Entities: Chemical Disease

Mesh：

Substances：
Aldehydes
Silanes

Year: 2006 PMID： 16986920 PMCID： PMC2720632 DOI： 10.1021/ol061579u

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

17 in total

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

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

2. Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts.

Authors: Yasuhiro Yamashita; Haruro Ishitani; Haruka Shimizu; Shū Kobayashi
Journal: J Am Chem Soc Date: 2002-04-03 Impact factor: 15.419

3. Nickel-catalyzed cyclizations and couplings with vinylzirconium reagents.

Authors: Yike Ni; Kande K D Amarasinghe; John Montgomery
Journal: Org Lett Date: 2002-05-16 Impact factor: 6.005

4. Nickel-catalyzed cyclizations, couplings, and cycloadditions involving three reactive components.

Authors: J Montgomery
Journal: Acc Chem Res Date: 2000-07 Impact factor: 22.384

5. Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes.

Authors: Karen M Miller; Timothy F Jamison
Journal: J Am Chem Soc Date: 2004-12-01 Impact factor: 15.419

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

Authors: Torsak Luanphaisarnnont; Chudi O Ndubaku; Timothy F Jamison
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

7. Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters.

Authors: D J Dixon; S V Ley; A Polara; T Sheppard
Journal: Org Lett Date: 2001-11-15 Impact factor: 6.005

Review 8. Nickel-catalyzed reductive cyclizations and couplings.

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

9. Studies in macrolide antibiotic synthesis: the role of tethered alkoxides in titanium alkoxide-mediated regioselective reductive coupling reactions.

Authors: Adilah B Bahadoor; Glenn C Micalizio
Journal: Org Lett Date: 2006-03-16 Impact factor: 6.005

10. Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors: Gireesh M Mahandru; Gang Liu; John Montgomery
Journal: J Am Chem Soc Date: 2004-03-31 Impact factor: 15.419

13 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. 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

6. 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

7. Convergent synthesis of piperidines by the union of conjugated alkynes with imines: a unique regioselective bond construction for heterocycle synthesis.

Authors: Ming Z Chen; Glenn C Micalizio
Journal: Org Lett Date: 2009-11-05 Impact factor: 6.005

8. Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes.

Authors: Ryan M Moslin; Karen Miller-Moslin; Timothy F Jamison
Journal: Chem Commun (Camb) Date: 2007-07-03 Impact factor: 6.222

9. Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones.

Authors: Thomas N Tekavec; Janis Louie
Journal: J Org Chem Date: 2008-03-05 Impact factor: 4.354

10. The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors: Allan U Barlan; Glenn C Micalizio
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457