Literature DB >> 15040750

Transformation of an optically active decahydro-6-isoquinolone scaffold: perfect Felkin-Anh diastereoselectivity.

Jens Christoffers1, Heiko Scharl, Wolfgang Frey, Angelika Baro.   

Abstract

Diastereomerically and enantiomerically pure decahydro-6-isoquinolone derivative 7 (>99% de, 97% ee) was obtained from the Michael addition product 3. Interestingly, aldehyde 7 reacted with a number of different Grignard reagents to give the secondary alcohols 9 in good yields as single diastereomers. This result can be explained by taking the Felkin-Anh model into account.

Entities:  

Year:  2004        PMID： 15040750     DOI： 10.1021/ol049831q

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


  3 in total

1.  Cytotoxicity of thiazolidinedione-, oxazolidinedione- and pyrrolidinedione-ring containing compounds in HepG2 cells.

Authors:  Alyssa M Keil; Douglas M Frederick; Erina Y Jacinto; Erica L Kennedy; Randy J Zauhar; Nathan M West; Ruy Tchao; Peter J Harvison
Journal:  Toxicol In Vitro       Date:  2015-07-17       Impact factor: 3.500

2.  Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides.

Authors:  Nicole D Bartolo; Krystyna M Demkiw; Jacquelyne A Read; Elizabeth M Valentín; Yingying Yang; Alexandra M Dillon; Chunhua T Hu; Michael D Ward; K A Woerpel
Journal:  J Org Chem       Date:  2022-02-15       Impact factor: 4.198

Review 3.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.