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Literature DB >> 19775184

Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

Abstract

Enantioenriched allenylsilanes are used as carbon nucleophiles in three-component reactions with in situ generated N-sulfonylimines to selectively form syn-homopropargylic sulfonamides. The reactions proceed with a variety of aldehyde and sulfonamide reaction partners. These novel reaction products are obtained with useful levels of diastereoselectivity, and the axial chirality of the allenylsilane is fully transferred to point chirality, forming products with >97% ee.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19775184 PMCID： PMC2906238 DOI： 10.1021/ol901692n

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

11 in total

1. Stereoselective synthesis of stereotriad subunits of polyketides through additions of nonracemic allenylsilanes to (R)- and (S)-2-methyl-3-oxygenated propanals

Authors:
Journal: J Org Chem Date: 2000-01-28 Impact factor: 4.354

2. Iodine as a very powerful catalyst for three-component synthesis of protected homoallylic amines.

Authors: Prodeep Phukan
Journal: J Org Chem Date: 2004-05-28 Impact factor: 4.354

3. Some typical advances in the synthetic applications of allenes.

Authors: Shengming Ma
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

4. Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: enantioselective synthesis of homoallylic carbamates.

Authors: Darren J Lipomi; James S Panek
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

5. Cu(I)-catalyzed enantioselective [3 + 2] cycloaddition reaction of 1-alkylallenylsilane with alpha-imino ester: asymmetric synthesis of dehydroproline derivatives.

Authors: Kazunori Daidouji; Kohei Fuchibe; Takahiko Akiyama
Journal: Org Lett Date: 2005-03-17 Impact factor: 6.005

6. Beta-silylated homopropargylic amines via the asymmetric allenylboration of aldimines.

Authors: Ana Z Gonzalez; John A Soderquist
Journal: Org Lett Date: 2007-02-13 Impact factor: 6.005

7. Enantioselective friedel-crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent.

Authors: Seiji Shirakawa; Richard Berger; James L Leighton
Journal: J Am Chem Soc Date: 2005-03-09 Impact factor: 15.419

8. Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Authors: Ryan A Brawn; James S Panek
Journal: Org Lett Date: 2009-01-15 Impact factor: 6.005

9. Preparation and use of enantioenriched allenylsilanes for the stereoselective synthesis of homopropargylic ethers.

Authors: Ryan A Brawn; James S Panek
Journal: Org Lett Date: 2007-06-09 Impact factor: 6.005

10. Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles.

Authors: Richard Berger; Philippe M A Rabbat; James L Leighton
Journal: J Am Chem Soc Date: 2003-08-13 Impact factor: 15.419

6 in total

5. Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors: Francois Grillet; Kay M Brummond
Journal: J Org Chem Date: 2013-03-29 Impact factor: 4.354

6. Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors: Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal: ARKIVOC Date: 2018-11-26 Impact factor: 1.140