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Search for "asymmetric (aza)-Reformatsky reaction" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Recent developments in the asymmetric Reformatsky-type reaction

Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21

based on the use of chiral substrates and enantioselective catalytic procedures. Keywords: asymmetric (aza)-Reformatsky reaction; asymmetric synthesis; chirality; diastereoselectivity; enantioselectivity; total synthesis; Introduction The Reformatsky reaction involves the formation of β

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Graphical Abstract

Scheme 1: Reformatsky-type reaction.

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Scheme 2: First total synthesis of prunustatin A based on a Zn-mediated Reformatsky reaction [17].

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Scheme 3: Synthesis of a γ-hydroxylysine derivative through a Zn-mediated nitrile Reformatsky-type reaction [18].

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Scheme 4: Synthesis of apratoxin E and its C30 epimer through a Zn-mediated Reformatsky reaction. Fmoc = 9-fl...

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Scheme 5: Synthesis of the eastern fragment of jatrophane diterpene Pl-3 through a SmI₂-mediated Reformatsky ...

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Scheme 6: First total synthesis of prebiscibactin through a SmI₂-mediated Reformatsky reaction. Boc = tert-bu...

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Scheme 7: Synthesis of prostaglandin E₂ methyl ester through a SmI₂-mediated Reformatsky reaction [23].

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Scheme 8: Synthesis of the C1–C11 fragment of tedanolide C through a SnCl₂-mediated Reformatsky reaction. PMB...

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Scheme 9: Synthesis of β-trifluoromethyl β-(N-tert-butylsulfinyl)amino esters exhibiting a quaternary stereoc...

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Scheme 10: Synthesis of α,α-difluoro-β-(N-tert-butylsulfinyl)amino esters through Zn(II)-mediated aza-Reformat...

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Scheme 11: Synthesis of a common fragment to anti-apoptotic protein inhibitors through a Zn-mediated aza-Refor...

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Scheme 12: Synthesis of α,α-difluoro-β-(N-tert-butylsulfinyl)amino ketones through a Zn-mediated aza-Reformats...

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Scheme 13: Synthesis of (2-oxoindolin-3-yl)amino esters through a Zn-mediated aza-Reformatsky reaction [30].

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Scheme 14: Synthesis of a precursor of sacubitril through a Zn-mediated aza-Reformatsky reaction [31].

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Scheme 15: Synthesis of epothilone D through a Cr(II)-mediated Reformatsky reaction. TFA = trifluoroacetic aci...

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Scheme 16: Synthesis of β-hydroxy-α-methyl-δ-trichloromethyl-δ-valerolactone through a Sm(II)- or Yb(II)-media...

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Scheme 17: Synthesis of cebulactam A1 through a Sm(II)-mediated Reformatsky reaction. MOM = methoxymethyl [34].

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Scheme 18: Synthesis of ansamacrolactams (+)-Q-1047H-A-A and (+)-Q-1047H-R-A through a Sm(II)-mediated Reforma...

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Scheme 19: Reformatsky reaction of aldehydes with ethyl iodoacetate in the presence of a chiral 1,2-amino alco...

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Scheme 20: Reformatsky reaction of aldehydes with ethyl bromoacetate in the presence of a chiral amide ligand [44]....

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Scheme 21: Reformatsky reaction of cinnamaldehyde with ethyl bromozinc-α,α-difluoroacetate in the presence of ...

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Scheme 22: Reformatsky reaction of aldehydes with an enolate equivalent prepared from phenyl isocyanate and CH₂...

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Scheme 23: Domino aza-Reformatsky/cyclization reactions of imines with ethyl dibromofluoroacetate in the prese...

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Scheme 24: Domino aza-Reformatsky/cyclization reactions of imines with ethyl bromodifluoroacetate in the prese...

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Scheme 25: Aza-Reformatsky reactions of cyclic imines with ethyl iodoacetate in the presence of a chiral diary...

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Scheme 26: Mechanism for aza-Reformatsky reaction of cyclic imines with ethyl iodoacetate in the presence of a...

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Scheme 27: Aza-Reformatsky reaction of dibenzo[b,f][1,4]oxazepines and dibenzo[b,f][1,4]thiazepine with ethyl ...

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Review

Published 02 Feb 2018

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