Journal Article10.1016/J.TET.2011.03.030
Development of an N-sulfinyl prolinamide for the asymmetric aldol reaction
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TL;DR: In this article, a new class of organocatalysts was reported that incorporated an N-sulfinyl amide in place of the carboxylic acid of proline to serve as a hydrogen bond donor, chiral directing group, and solubilizing element.
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About: This article is published in Tetrahedron. The article was published on 17 Jun 2011. The article focuses on the topics: Organocatalysis & Aldol reaction.
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Citations
Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis
TL;DR: This Review provides comprehensive and critical information on the plethora of sulfur-based chiral ligands and organocatalysts used in asymmetric synthesis, which have been published within the last 15 years, but is confined to the presentation of only those chiral catalysts/ligands that possess a stereogenic sulfur atom.
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Catalytic enantioselective aldol reactions
TL;DR: This review article is organized under the categories of catalytic enantioselective aldol reactions of preformed enolates, catalyticEnantioseLECTive direct-type a Aldol reactions using chiral metal catalysts, and catalytic Enantioselections in aqueous media.
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Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.
TL;DR: This review is devoted to the modern methods of preparation of sulfinyl derivatives in enantiopure or enantiomerically enriched form.
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Hydrogen‐Bonding in Aminocatalysis: From Proline and Beyond
TL;DR: This Concept article summarizes recent progress in the field of hydrogen-bonding aminocatalysis using proline-derived systems and discusses both mono- and double-hydrogen- bonding motifs.
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Catalytic enantioselective protonation of nitronates utilizing an organocatalyst chiral only at sulfur.
TL;DR: This work represents the first enantioselective catalytic addition of any type of nucleophile to this class of nitroalkenes and a new type of N-sulfinyl urea catalyst with chirality residing only at the sulfinyl group was developed, thereby enabling the incorporation of a diverse range of achiral diamine motifs.
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References
Proline-Catalyzed Direct Asymmetric Aldol Reactions
TL;DR: The finding that the amino acid proline is an effective asymmetric catalyst for the direct aldol reaction between unmodified acetone and a variety of aldehydes is reported.
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Synthesis and Applications of tert-Butanesulfinamide
TL;DR: Amino Acid Derivatives: Synthesis of R-Substituted Organometallic Reagents to N-tert-Butanesulfinyl Imines 3687 * E-mail: jellman@berkeley.edu.
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The Direct Catalytic Asymmetric Aldol Reaction
TL;DR: This critical review documents the development of direct catalytic asymmetric aldol methodologies, including organocatalytic and metal-based strategies, which have improved the reactivity, selectivity and substrate scope of the direct a Aldol reaction and enabled the synthesis of complex molecular targets.
Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
TL;DR: Tetrazole and acylsulfonamide organocatalysts derived from proline have been synthesised and applied to the asymmetric Mannich, nitro-Michael and aldol reactions to give results that are superior to the proline-catalysed counterpart.
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