Literature DB >> 24506346

Enantioselective desymmetrization of diesters.

Jennifer Wilent1, Kimberly S Petersen.   

Abstract

The desymmetrization of prochiral diesters with a chiral phosphoric acid catalyst to produce highly enantioenriched lactones in excellent yield is reported. The process is easily scaled and accommodates a variety of substitution patterns, many of which result in the generation of an enantioenriched all-carbon quaternary center. Manipulation of lactone product to useful small building blocks is also described.

Entities:  

Year:  2014        PMID: 24506346     DOI: 10.1021/jo402853v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization.

Authors:  Jennifer E Wilent; Ghassan Qabaja; Kimberly S Petersen
Journal:  Organic Synth       Date:  2016

2.  Synthesis of Structurally Diverse 3-, 4-, 5-, and 6-Membered Heterocycles from Diisopropyl Iminomalonates and Soft C-Nucleophiles.

Authors:  Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  J Org Chem       Date:  2019-05-14       Impact factor: 4.354

Review 3.  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

4.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

5.  Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations.

Authors:  Alan R Burns; Amaël G E Madec; Darryl W Low; Iain D Roy; Hon Wai Lam
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825

  5 in total

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