Literature DB >> 12027655

Asymmetric construction of quaternary centers by enantioselective allylation: application to the synthesis of the serotonin antagonist LY426965.

Scott E Denmark1, Jiping Fu.   

Abstract

[reaction: see text] Catalytic enantioselective allylation with a chiral bisphosphoramide was applied to the synthesis of LY426965, a serotonin antagonist. The key step, addition of a 3,3-disubstituted allyltrichlorosilane to benzaldehyde, provided the adduct containing a stereogenic quaternary center with excellent diastereoselectivity and enantioselectivity.

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Year:  2002        PMID: 12027655     DOI: 10.1021/ol025971t

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


  12 in total

1.  Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process.

Authors:  T Andrew Mitchell; Cunxiang Zhao; Daniel Romo
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

2.  (R)-3-METHYL-3-PHENYL-1-PENTENE VIA CATALYTIC ASYMMETRIC HYDROVINYLATION.

Authors:  Craig R Smith; Aibin Zhang; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Min Xie
Journal:  Organic Synth       Date:  2008

3.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

4.  Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.

Authors:  Jacob C Green; Joseph M Zanghi; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-01-17       Impact factor: 15.419

5.  Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors:  Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal:  Chemistry       Date:  2011-06-03       Impact factor: 5.236

6.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Authors:  Laura T Kliman; Scott N Mlynarski; Grace E Ferris; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-01       Impact factor: 15.336

7.  Amplification of anti-diastereoselectivity via Curtin-Hammett effects in ruthenium-catalyzed hydrohydroxyalkylation of 1,1-disubstituted allenes: diastereoselective formation of all-carbon quaternary centers.

Authors:  Jason R Zbieg; Emma L McInturff; Joyce C Leung; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-12-22       Impact factor: 15.419

8.  Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

Authors:  Barry M Trost; Julien P N Papillon; Thomas Nussbaumer
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

9.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

10.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

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