Literature DB >> 12943386

Synthesis of enantioenriched propargylic alcohols related to polyketide natural products. A comparison of methodologies.

James A Marshall1, Matthew P Bourbeau.   

Abstract

[reaction: see text] Applications of methodology for the synthesis of propargylic alcohols related to polyketide natural products were examined. Noyori's asymmetric transfer hydrogenation of alpha-chiral alkynones was found to be highly selective and catalyst controlled. Additions of TMS acetylene to alpha-chiral aldehydes, catalyzed by a Ti(O-i-Pr)(4)-BINOL complex, were diastereoselective but substrate dependent.

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Year:  2003        PMID： 12943386     DOI： 10.1021/ol034918h

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


  12 in total

1.  Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.

Authors:  Gretchen R Stanton; Meara C Kauffman; Patrick J Walsh
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

Review 2.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

3.  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

4.  Overriding Felkin control: a general method for highly diastereoselective chelation-controlled additions to alpha-silyloxy aldehydes.

Authors:  Gretchen R Stanton; Corinne N Johnson; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

5.  Highly diastereoselective chelation-controlled additions to α-silyloxy ketones.

Authors:  Gretchen R Stanton; Gamze Koz; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-05-02       Impact factor: 15.419

6.  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 7.  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

8.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

9.  Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus.

Authors:  Hau-Heredia Lenin; Figueroa-Valverde Lauro; Rosas-Nexticapa Marcela; Herrera-Meza Socorro; López-Ramos Maria; Díaz-Cedillo Francisco; García-Cervera Elodia; Pool-Gómez Eduardo; Paat-Estrella Josefa; Cauich-Carrillo Regina; Euan-Hau Saidy
Journal:  J Chem Biol       Date:  2017-06-08

10.  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
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