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Enantioselective Synthesis of β-Amino Acids.

Enantioselective synthesis of α, β-disubstituted-β-amino acids.

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Enantioselective synthesis of alpha-fluorinated beta2-amino acids.

The enantioselective synthesis of (−)-pavidolide B (1) was achieved in a linear sequence of 10 steps. The key steps are (a) an enantioselective organocatalytic cyclopropanation; (b) a radical-based cascade annulation for the regio- and diastereo-selective synthesis of the highly functionalized lactone 3 bearing the characteristic tricyclic core and seven contiguous stereocenters; (c) a sequential ring-closing metathesis reaction and a RhCl3-catalyzed double bond isomerization to form the seven-membered D ring of (−)-pavidolide B.

Enantioselective synthesis of α, b-substituted β-amino acids.

The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp^3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.

Enantioselective Chemical Synthesis

A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind–Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C–C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet–Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.

Highly enantioselective organocatalytic addition of unmodified aldehydes to N-Boc protected imines: One-pot asymmetric synthesis of β-amino acids.

Organocatalytic enantioselective conjugate addition to alkynones.

Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol.

Written by world-renowned and best-selling experts, Nobel Laureate E. J. Corey and Laszlo Kurti, Enantioselective Chemical Synthesis offers an authoritative and comprehensive overview of the field's progress; the processes and tools for key formations; future development for complex, stereocontrolled (enantiomeric or diastereoisomeric) molecules; and valuable examples of multi-step syntheses. Utilizing a color-coded scheme to illustrate chemical transformations, Enantioselective Chemical Synthesis provides clear explanation and guidance through vital asymmetrical syntheses and insight into the next steps for the field. Researchers, professionals, and academics will benefit from this valuable, thorough, and unique resource.

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  • Enantiospecific Total Syntheses of Kapakahines B and F, J.

    Direct catalytic enantioselective Mannich reactions: Synthesis of protected anti-α, β-diamino acids.

  • Short, Enantioselective Total Synthesis of Stephacidin A, Angew.

    Direct catalytic enantioselective Mannich reactions: Synthesis of protected anti-α, β-diamino acids.

  • A Short, Enantioselective Total Synthesis of Okaramine N, J.

    Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

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Enantioselective synthesis - Wikipedia

and and and (2016) Enantioselective Total Synthesis of (+)-Psiguadial B. Journal of the American Chemical Society, 138 (31). pp. 9803-9806. ISSN 0002-7863.

Enantioselective Synthesis of (+)-Peganumine A - …

Part 1
Tools for enantioselective synthesis Tools for enantioselective synthesis Formation of C-H Bonds Formation of C-O Bonds Addition of H-Y (Y=B, Si, CO, CN, vinyl) to C=C Formation of C-C Bonds Cyclization Part 2
Planning enantioselective syntheses Part 3
Enantioselective multi-step synthesis: examples

Enantioselective Chemical Synthesis - 1st Edition

A straightforward and atom-economical enantioselective approach to highly substituted tetrahydropyrans is reported. The process, which consists of an intermolecular gold-catalyzed [2+2+2] cycloaddition between allenamides, alkenes, and aldehydes, is efficiently catalyzed by both phosphoramidite- and chiral -heterocyclic carbene-gold catalysts, occurs with complete chemoselectivity and regioselectivity, moderate diastereoselectivity, and moderate to very good enantioselectivities.

Purchase Enantioselective Chemical Synthesis - 1st Edition

Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids.

Enantioselective Chemical Synthesis - ScienceDirect

The Johnson Group at UNC Chapel Hill focuses on new reaction development, enantioselective catalysis, and natural product synthesis.

The online version of Enantioselective Chemical Synthesis by Elias J

Enantioselective synthesis of β-amino esters bearing a benzothiazole moiety via a Mannich-type reaction catalyzed by a cinchona alkaloid derivative.

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