Literature DB >> 11009360

An efficient chiral moderator prepared from inexpensive (+)-3-carene: synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963.

G S Kauffman1, G D Harris, R L Dorow, B R Stone, R L Parsons, J A Pesti, N A Magnus, J M Fortunak, P N Confalone, W A Nugent.   

Abstract

The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by addition of morpholine to alpha-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.

Entities:  

Mesh：

Substances：

Year:  2000        PMID： 11009360     DOI： 10.1021/ol006321x

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


  11 in total

1.  Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines.

Authors:  Chunmei Wei; Joel T Mague; Chao-Jun Li
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

2.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

3.  Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.

Authors:  Janis Jermaks; Evan H Tallmadge; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2018-02-19       Impact factor: 15.419

4.  Lithium hexamethyldisilazide-mediated enolizations: influence of triethylamine on E/Z selectivities and enolate reactivities.

Authors:  Peter F Godenschwager; David B Collum
Journal:  J Am Chem Soc       Date:  2008-06-17       Impact factor: 15.419

5.  Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines.

Authors:  Carolin Edinger; Jörn Kulisch; Siegfried R Waldvogel
Journal:  Beilstein J Org Chem       Date:  2015-02-27       Impact factor: 2.883

6.  Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.

Authors:  Matthias Wünsch; David Schröder; Tanja Fröhr; Lisa Teichmann; Sebastian Hedwig; Nils Janson; Clara Belu; Jasmin Simon; Shari Heidemeyer; Philipp Holtkamp; Jens Rudlof; Lennard Klemme; Alessa Hinzmann; Beate Neumann; Hans-Georg Stammler; Norbert Sewald
Journal:  Beilstein J Org Chem       Date:  2017-11-15       Impact factor: 2.883

7.  Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

Authors:  Ziyi Li; Li Wang; Yunqi Huang; Haibo Mei; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2020-10-29       Impact factor: 2.883

8.  A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolines via intramolecular aza-Michael reaction to α,β-unsaturated esters.

Authors:  Guanglong Su; Connor J Thomson; Ken Yamazaki; Daniel Rozsar; Kirsten E Christensen; Trevor A Hamlin; Darren J Dixon
Journal:  Chem Sci       Date:  2021-03-18       Impact factor: 9.825

9.  Solution structures of lithium amino alkoxides used in highly enantioselective 1,2-additions.

Authors:  Angela M Bruneau; Lara Liou; David B Collum
Journal:  J Am Chem Soc       Date:  2014-02-05       Impact factor: 15.419

10.  Synthesis of Propargylamines via Michael Addition Using Methyl Vinyl Ketone Derivatives, 1-Alkynes, and Secondary Amines Catalyzed by Copper (I) Halides.

Authors:  Bantu Udaykumar; Mariappan Periasamy
Journal:  ACS Omega       Date:  2019-12-02
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.