Literature DB >> 21319834

Highly enantioselective direct vinylogous Michael addition of γ-butenolide to enals.

Adrien Quintard1, Alice Lefranc, Alexandre Alexakis.   

Abstract

An unprecedented and simple direct vinylogous addition of deconjugated butenolide to enals has been developed in excellent stereoselectivities (>95% ee), with Aminal-PYrrolidine (APY) catalyst. This methodology allows for the efficient preparation of complex γ-butenolide from readily available renewable resources. Furthermore, preliminary mechanistic investigations have allowed for the better understanding of the origin of both stereoselectivities and of the observed high reactivities.

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Year:  2011        PMID: 21319834     DOI: 10.1021/ol200235j

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


  5 in total

1.  Control of chemoselectivity in asymmetric tandem reactions: Direct synthesis of chiral amines bearing nonadjacent stereocenters.

Authors:  Zhe Li; Bin Hu; Yongwei Wu; Chao Fei; Li Deng
Journal:  Proc Natl Acad Sci U S A       Date:  2018-02-05       Impact factor: 11.205

2.  Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors:  Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-23       Impact factor: 15.336

3.  Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.

Authors:  Jessica A Griswold; Matthew A Horwitz; Leslie V Leiva; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2017-02-06       Impact factor: 4.354

Review 4.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

5.  5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene.

Authors:  Marta Romaniszyn; Lesław Sieroń; Łukasz Albrecht
Journal:  J Org Chem       Date:  2022-03-29       Impact factor: 4.198

  5 in total

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