Simple access to 2-methylalk-2-enoates and insect pheromones by zinc-promoted reduction of Baylis–Hillman-derived allylic bromides

Fernandes, Luciano; Bortoluzzi, Adaı́lton J.; Sá, Marcus M.

doi:10.1016/j.tet.2004.08.018

Cited by 44 publications

(18 citation statements)

References 51 publications

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“…Compounds 1a,b,e,f,g,i,k,l showed physical and spectral data in accordance with their expected structure and by comparison with data in literature. 8,11,18,[20][21][22][23][24][25] Methyl (Z)-2-(bromomethyl)-3-(4-methoxyphenyl) …”

Section: Methyl 3-hydroxy-2-methylene-3-(2-chlorophenyl) Propanoate (2g)mentioning

confidence: 99%

“…Allylic bromides 1 are versatile building blocks of many important substances including natural products, heterocycles and biologically-active molecules [1][2][3][4][5][6][7][8][9][10][11][12][13] (Scheme 1). These multifunctional compounds can be prepared from α-methylene-β-hydroxyesters 2, which are easily obtained by the well-recognized Morita-BaylisHillman reaction.…”

Section: Introductionmentioning

confidence: 99%

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A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts

Ferreira¹,

Fernandes²,

Sá³

2009

J. Braz. Chem. Soc.

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(Z)-2-(Bromometil)-2-alcenoatos são importantes intermediários sintéticos e foram preparados de forma simples e prática pelo tratamento de α-metileno-β-hidroxiésteres (produtos da reação de Morita-Baylis-Hillman) com LiBr/H 2 SO 4 em acetonitrila à temperatura ambiente. Além de fornecer altos rendimentos e de tolerar a presença de diversos grupos funcionais, esta nova metodologia utiliza reagentes baratos e não faz uso de HBr.Representative (Z)-2-(bromomethyl)-2-alkenoates were easily prepared in high yield by treating α-methylene-β-hydroxyesters (Morita-Baylis-Hillman adducts) with LiBr/H 2 SO 4 in acetonitrile at room temperature. Besides the tolerance to many diverse functional groups, this new methodology employs inexpensive reagents and avoids the use of HBr.

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Section: Methyl 3-hydroxy-2-methylene-3-(2-chlorophenyl) Propanoate (2g)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts

Ferreira¹,

Fernandes²,

Sá³

2009

J. Braz. Chem. Soc.

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“…124 Fernandes et al 125 described a synthesis of 37 in 39% overall yield and high stereoselectivity by zinc-promoted reduction of 2-(bromomethyl) alkenoates derived from Baylis-Hillman adducts (Scheme 38). …”

Section: (E)-24-dimethyl-2-hexenoic Acid (37)mentioning

confidence: 99%

Insect pheromone synthesis in Brazil: an overview

Zarbin¹,

Villar²,

Corrêa³

2007

J. Braz. Chem. Soc.

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Nesta revisão estão descritas as sínteses de feromônios de insetos desenvolvidas e publicadas por grupos de pesquisa brasileiros, e tem por objetivo apresentar o estado da arte desta área de pesquisa no país e fornecer uma informação rápida sobre as moléculas já sintetizadas e metodologias empregadas. As sínteses estão apresentadas em ordem cronológica, exceto quando se trata de diferentes metodologias para a mesma molécula.This review describes the syntheses of insect pheromones developed and published by Brazilian research groups and aims to present the state of the art of this area in the country, and also to serves as a quick view of the already synthesized molecules and employed methodology. The syntheses are presented in chronological order, except when they refer to different approaches for the same molecule.

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“…Success was ultimately realized by first converting the allylic acetates into their corresponding bromides under acidic conditions and subsequentreduction with NaBH 3 CN in DMF. [20] Thus, am ixture of 12 and 13 was treated sequentially with 33 %H Br followed by NaBH 3 CN to give (À)-sungucine (1)a nd (À)-isosungucine (2)i n4 0-50 %o verall yield following chromatographic separation. Spectra data for 1 and 2 (e.g., 1 Ha nd 13 CNMR, IR) were in complete agreement with the reported values.…”

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confidence: 99%

Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine

Zhao

Teijaro

Chen

et al. 2016

Chemistry A European J

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The first chemical syntheses of complex, bis-Strychnos alkaloids (-)-sungucine (1), (-)-isosungucine (2), and (-)-strychnogucine B (3) from (-)-strychnine (4) is reported. Key steps included (1) the Polonovski-Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3 CN-mediated reduction to fashion the ethylidene moieties in 1-3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.

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Simple access to 2-methylalk-2-enoates and insect pheromones by zinc-promoted reduction of Baylis–Hillman-derived allylic bromides

Cited by 44 publications

References 51 publications

A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts

A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts

Insect pheromone synthesis in Brazil: an overview

Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine

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