Literature DB >> 11150207

Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes: preparation of 3-hydroxy-1-butynes

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Abstract

We report the first example of enantioselective aldehyde additions of 2-methyl-3-butyn-2-ol, a commodity bulk chemical that is readily available. Following a facile fragmentation reaction, the addition reactions provide access to optically active terminal acetylenes as useful building blocks for asymmetric synthesis.

Entities:  

Year:  2000        PMID： 11150207     DOI： 10.1021/ol006791r

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


  14 in total

1.  Density functional computations of enantioselective alkynylation of aldehyde catalyzed by chiral zinc(II)-complexes.

Authors:  Qingxi Meng; Ming Li; Jinsheng Zhang
Journal:  J Mol Model       Date:  2006-01-14       Impact factor: 1.810

2.  Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.

Authors:  Barry B Snider; Jingye Zhou
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

3.  Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors:  Blane P Zavesky; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-20       Impact factor: 15.336

4.  Identification of an Unexpected 2-Oxonia[3,3]sigmatropic Rearrangement/Aldol Pathway in the Formation of Oxacyclic Rings. Total Synthesis of (+)-Aspergillin PZ.

Authors:  Stephen M Canham; Larry E Overman; Paul S Tanis
Journal:  Tetrahedron       Date:  2011-09-19       Impact factor: 2.457

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

6.  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

7.  Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors:  Gary A Molander; Erin M Sommers; Sharon R Baker
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354

8.  Infrared spectroscopic investigations on the metallation of terminal alkynes by Zn(OTf)2.

Authors:  Roger Fässler; Craig S Tomooka; Doug E Frantz; Erick M Carreira
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

9.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

10.  Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419
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