Literature DB >> 12790541

Highly stereoselective anti SN2' substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents.

Nicole Harrington-Frost1, Helena Leuser, M Isabel Calaza, Florian F Kneisel, Paul Knochel.   

Abstract

[reaction: see text] Allylic substitution reactions of zinc-copper organometallics on (Z)-allylic pentafluorobenzoates proceed with very high regioselectivity and excellent anti selectivity. The high fidelity in transfer of stereochemical information allowed a short synthesis of (+)-ibuprofen (97% ee).

Entities:  

Year:  2003        PMID： 12790541     DOI： 10.1021/ol034525i

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


  13 in total

1.  Ruthenium-Catalyzed C-H Allylation of Alkenes with Allyl Alcohols via C-H Bond Activation in Aqueous Solution.

Authors:  Xiaowei Wu; Haitao Ji
Journal:  J Org Chem       Date:  2018-09-21       Impact factor: 4.354

2.  Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters.

Authors:  Kelsey M Cobb; Javon M Rabb-Lynch; Megan E Hoerrner; Alex Manders; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2017-08-07       Impact factor: 6.005

3.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

4.  Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

5.  Zirconium-mediated SN2' substitution of allylic ethers: regio- and stereospecific formation of protected allylic amines.

Authors:  Gojko Lalic; Suzanne A Blum; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2005-12-07       Impact factor: 15.419

6.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

7.  Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens.

Authors:  Jacob A Friest; Yukari Maezato; Sylvain Broussy; Paul Blum; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

8.  Catalytic asymmetric synthesis using feedstocks: an enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes.

Authors:  Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

9.  Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols.

Authors:  Xiaowei Wu; Haitao Ji
Journal:  Org Lett       Date:  2018-03-27       Impact factor: 6.005

10.  Divalent and Multivalent Activation in Phosphate Triesters: A Versatile Method for the Synthesis of Advanced Polyol Synthons.

Authors:  Christopher D Thomas; James P McParland; Paul R Hanson
Journal:  European J Org Chem       Date:  2009-10-08
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.