Literature DB >> 12423107

Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.

Ge Gao1, David Moore, Ru-Gang Xie, Lin Pu.   

Abstract

The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction. [reaction: see text]

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Year:  2002        PMID： 12423107     DOI： 10.1021/ol026921r

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


  13 in total

1.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors:  Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

3.  Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers.

Authors:  Bin Sui; Edmund A-H Yeh; Dennis P Curran
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

4.  Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol.

Authors:  Barry M Trost; Adrien Quintard
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-05       Impact factor: 15.336

5.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

Review 6.  Isolation, biology and chemistry of the disorazoles: new anti-cancer macrodiolides.

Authors:  Chad D Hopkins; Peter Wipf
Journal:  Nat Prod Rep       Date:  2009-03-11       Impact factor: 13.423

7.  1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes.

Authors:  Qin Wang; Shan-Yong Chen; Xiao-Qi Yu; Lin Pu
Journal:  Tetrahedron       Date:  2007-05-21       Impact factor: 2.457

8.  Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.

Authors:  Ge Gao; Ru-Gang Xie; Lin Pu
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-16       Impact factor: 11.205

9.  Enantioselective total synthesis of the potent antitumor agent (-)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure; Alexei Polosukhin; Hai-Ren Zhang
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

10.  Continuous-flow hydration-condensation reaction: Synthesis of α,β-unsaturated ketones from alkynes and aldehydes by using a heterogeneous solid acid catalyst.

Authors:  Magnus Rueping; Teerawut Bootwicha; Hannah Baars; Erli Sugiono
Journal:  Beilstein J Org Chem       Date:  2011-12-15       Impact factor: 2.883
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