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Literature DB >> 22928846

Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines.

Quan Cai¹, Chuan Liu, Xiao-Wei Liang, Shu-Li You.

Abstract

Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines has been realized. With 5 mol % of chiral phosphoric acid, enantioenriched pyrroloindoline derivatives were obtained in good yields and enantioselectivity (up to 95% yield and 83% ee) from readily available tryptamines and enones.

Entities: Chemical

Mesh：

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Year: 2012 PMID： 22928846 DOI： 10.1021/ol302043s

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

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Cited

8 in total

1. Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

Authors: Ryan R Walvoord; Marisa C Kozlowski
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

2. Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors: Arijit A Adhikari; Léa Radal; John D Chisholm
Journal: Synlett Date: 2017-07-11 Impact factor: 2.454

3. Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Authors: Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal: J Am Chem Soc Date: 2013-04-03 Impact factor: 15.419

4. Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors: Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2014-04-08 Impact factor: 15.336

5. Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors: Lindsay M Repka; Sarah E Reisman
Journal: J Org Chem Date: 2013-12-02 Impact factor: 4.354

Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines.

1. Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

2. Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

3. Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

4. Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

5. Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

6. Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

7. Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

8. Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations--New Method for the Synthesis of Pyrroloindolines.