Literature DB >> 16321015

Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.

Vijaya Bhasker Gondi1, Michel Gravel, Viresh H Rawal.   

Abstract

[chemical reaction: see text]. The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products in good yields and enantiomeric excesses.

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Year:  2005        PMID： 16321015      PMCID： PMC2537470          DOI： 10.1021/ol052301p

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


  18 in total

1.  Axially chiral amidinium ions as inducers of enantioselectivity in Diels-Alder reactions

Authors: 
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2.  Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts.

Authors:  Tomotaka Okino; Yasutaka Hoashi; Yoshiji Takemoto
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3.  Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.

Authors:  Scott E Denmark; Gregory L Beutner; Thomas Wynn; Martin D Eastgate
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

4.  Catalytic Asymmetric Vinylogous Mukaiyama-aldol (CAVM) reactions: the enolate activation.

Authors:  G Bluet; J M Campagne
Journal:  J Org Chem       Date:  2001-06-15       Impact factor: 4.354

5.  Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.

Authors:  Aditya K Unni; Norito Takenaka; Hisashi Yamamoto; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

Review 6.  Catalytic, enantioselective, vinylogous aldol reactions.

Authors:  Scott E Denmark; John R Heemstra; Gregory L Beutner
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-25       Impact factor: 15.336

7.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors:  Daisuke Uraguchi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

8.  Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding.

Authors:  Avinash N Thadani; Ana R Stankovic; Viresh H Rawal
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

9.  Lewis base activation of Lewis acids. Vinylogous aldol reactions.

Authors:  Scott E Denmark; Gregory L Beutner
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419

10.  Chiral proton catalysis: a catalytic enantioselective direct aza-Henry reaction.

Authors:  Benjamin M Nugent; Ryan A Yoder; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419
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4.  Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.

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Authors:  Mahmoud Nasrollahzadeh; Zahra Issaabadi; S Mohammad Sajadi
Journal:  RSC Adv       Date:  2018-08-02       Impact factor: 3.361

Review 8.  Chiral Diol-Based Organocatalysts in Enantioselective Reactions.

Authors:  Truong N Nguyen; Po-An Chen; Krit Setthakarn; Jeremy A May
Journal:  Molecules       Date:  2018-09-11       Impact factor: 4.411

9.  Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.

Authors:  Katharina Gratzer; Guddeangadi N Gururaja; Mario Waser
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  9 in total

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