Literature DB >> 27997201

A Palladium-Catalyzed Asymmetric Allylic Alkylation Approach to α-Quaternary γ-Butyrolactones.

Marllon Nascimento de Oliveira1, Jeremy Fournier1, Stellios Arseniyadis1, Janine Cossy1.   

Abstract

The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α'-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

Entities:  

Year:  2016        PMID: 27997201     DOI: 10.1021/acs.orglett.6b02971

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


  5 in total

1.  Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal.

Authors:  Carina I Jette; Z Jaron Tong; Ryan G Hadt; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-16       Impact factor: 15.336

2.  Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones.

Authors:  Eleanor Bowen; Gillian Laidlaw; Bethany C Atkinson; Timur A McArdle-Ismaguilov; Vilius Franckevičius
Journal:  J Org Chem       Date:  2022-07-08       Impact factor: 4.198

3.  Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Authors:  Aurapat Ngamnithiporn; Carina I Jette; Shoshana Bachman; Scott C Virgil; Brian M Stoltz
Journal:  Chem Sci       Date:  2018-01-24       Impact factor: 9.825

4.  Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides.

Authors:  Gillian Laidlaw; Vilius Franckevičius
Journal:  Org Lett       Date:  2021-12-16       Impact factor: 6.005

5.  Cu-catalyzed enantioselective synthesis of tertiary benzylic copper complexes and their in situ addition to carbonyl compounds.

Authors:  Fengchang Cheng; Wenxin Lu; Wei Huang; Lu Wen; Mingfeng Li; Fanke Meng
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

  5 in total

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