Literature DB >> 29711532

A Novel, Highly Enantioselective Ketone Alkynylation Reaction Mediated by Chiral Zinc Aminoalkoxides.

Lushi Tan1, Cheng-Yi Chen1, Richard D Tillyer1, Edward J J Grabowski1, Paul J Reider1.   

Abstract

Kilogram-scale synthesis of the HIV reverse transcriptase inhibitor efavirenz was achieved by means of a highly enantioselective alkynylation of prochiral ketones 1 with alkynyllithium or alkynylmagnesium reagents in the presence of chiral zinc aminoalkoxides as mediators. With the achiral auxiliary 2,2,2-trifluoroethanol (R3 =CF3 CH2 ), the efavirenz precursor 2 (R1 =H, R2 =cyclopropyl) was obtained with an ee of 99.2%. © 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Alkynylations; Amino alcohols; Ketones; Nucleophilic additions; Zinc

Year:  1999        PMID： 29711532     DOI： 10.1002/(SICI)1521-3773(19990301)38:5<711::AID-ANIE711>3.0.CO;2-W

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Selective interaction of the human immunodeficiency virus type 1 reverse transcriptase nonnucleoside inhibitor efavirenz and its thio-substituted analog with different enzyme-substrate complexes.

Authors:  G Maga; D Ubiali; R Salvetti; M Pregnolato; S Spadari
Journal:  Antimicrob Agents Chemother       Date:  2000-05       Impact factor: 5.191

2.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

3.  Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.

Authors:  Kevin T O'Brien; Amos B Smith
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

4.  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

5.  Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam.

Authors:  Václav Jurčík; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2011-06-06       Impact factor: 2.883

6.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

Authors:  Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

7.  Highly enantioselective addition of phenylethynylzinc to aldehydes catalyzed by chiral cyclopropane-based amino alcohols.

Authors:  Bing Zheng; Zhiyuan Li; Feipeng Liu; Yanhua Wu; Junjian Shen; Qinghua Bian; Shicong Hou; Ming Wang
Journal:  Molecules       Date:  2013-12-11       Impact factor: 4.411

8.  Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.

Authors:  Camilla Pfeffer; Patrick Probst; Nick Wannenmacher; Wolfgang Frey; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-19       Impact factor: 16.823
  8 in total

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