Literature DB >> 18808137

N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: a practical proline mimetic for facilitating enantioselective aldol reactions.

Hua Yang1, Rich G Carter.   

Abstract

A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitating enantioselective and diastereoselective aldol reactions with a range of substrates in nonpolar organic solvents in the presence of a single equivalent of water. Additionally, catalyst loading as low as 2 mol % can be employed in the absence of any organic solvent with continued high levels of selectivity.

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Year:  2008        PMID： 18808137      PMCID： PMC2587530          DOI： 10.1021/ol801941j

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


  25 in total

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4.  Highly efficient and reusable dendritic catalysts derived from N-prolylsulfonamide for the asymmetric direct aldol reaction in water.

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5.  Brønsted acids as additives for the direct asymmetric aldol reaction catalyzed by l-prolinethioamides. direct evidence for enamine-iminium catalysis.

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6.  Highly efficient asymmetric direct stoichiometric aldol reactions on/in water.

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7.  Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives.

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8.  Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water.

Authors:  Seiji Aratake; Takahiko Itoh; Tsubasa Okano; Norio Nagae; Tatsunobu Sumiya; Mitsuru Shoji; Yujiro Hayashi
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  5 in total

1.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

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Authors:  Hua Yang; Rich G Carter
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

3.  Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

Authors:  Hua Yang; Rich G Carter
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4.  Highly stereoselective and scalable anti-aldol reactions using N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and origins of stereoselectivities.

Authors:  Hua Yang; Subham Mahapatra; Paul Ha-Yeon Cheong; Rich G Carter
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

5.  Toward a unified approach for the lycopodines: synthesis of 10-hydroxylycopodine, deacetylpaniculine, and paniculine.

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  5 in total

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