Asymmetric synthesis of the carbapenem antibiotic (+)-PS-5

Shibasaki, Masakatsu; Ishida, Yuki; Iwasaki, Genji; Iimori, Toshifumi

doi:10.1021/jo00391a073

Cited by 76 publications

(10 citation statements)

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“…[13] [14] The boron enolate of S-phenyl thiobutanoate reacted with (S)α-methylbenzylamine derived imine 10 to afford a 62.5:25.0:12.5 mixture of β-amino S-thioesters in 69% yield. [13] [14] The boron enolate of S-phenyl thiobutanoate reacted with (S)α-methylbenzylamine derived imine 10 to afford a 62.5:25.0:12.5 mixture of β-amino S-thioesters in 69% yield.…”

Section: Boron Enolatesmentioning

confidence: 99%

The S-Thioester Enolate/Imine Condensation: A Shortcut to β-Lactams

Benaglia¹,

Cinquini²,

Cozzi³

2000

Eur. J. Org. Chem.

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Section: Boron Enolatesmentioning

confidence: 99%

The S-Thioester Enolate/Imine Condensation: A Shortcut to β-Lactams

Benaglia¹,

Cinquini²,

Cozzi³

2000

Eur. J. Org. Chem.

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“…To achieve the recyclability of the metal catalyst, Li [33] and Alper [34] used room-temperature ionic liquid-immobilized catalysts. However, ionic liquids, especially imidazolium-based systems containing BF 4 or PF 6 anions, are toxic in nature because they liberate hazardous HF, and their high cost and disposability make their utility limited. [35] Recently, Yun and co-workers also reviewed the environmental fate and toxicity of ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

Copper‐catalyzed one‐pot synthesis of propargylamines via CH activation in PEG

Zhang

Chen

Gao

et al. 2010

Applied Organom Chemis

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“…Propargylamines are important intermediates for the synthesis of polyfunctional amino derivatives as well as natural products and biologically active compounds 1 2 3 due to the rich chemistry associated with the alkynyl group 4 . Consequently, significant efforts have been devoted to develop methodologies for preparing this important class of compounds in enantiomerically enriched form.…”

mentioning

confidence: 99%

Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis

Wang

Zhu

et al. 2015

Nat Commun

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Propargylamines are important intermediates for the synthesis of polyfunctional amino derivatives and natural products and biologically active compounds. The classic method of synthesizing chiral propargylamines involves the asymmetric alkynylation of imines. Here, we report a significant advance in the catalytic asymmetric Mannich-type synthesis of propargylamines through catalytic asymmetric addition of carbon nucleophiles to C-alkynyl imines, culminating in a highly syn-selective catalytic asymmetric Mannich reaction of C-alkynyl imines that provide syn-configured propargylamines with two adjacent stereogenic centres and a transition metal-free organocatalytic asymmetric approach to β-alkynyl-β-amino acids with high efficiency and practicality, via a chiral Brønsted base-catalysed asymmetric Mannich-type reaction of in situ generated challenging N-Boc C-alkynyl imines from previously unreported C-alkynyl N-Boc-N,O-acetals, with α-substituted β-keto esters and less-acidic malonate (thio)esters as nucleophiles, respectively. A catalytic activation strategy is also disclosed, which may have broad implications for use in catalysis and synthesis.

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Asymmetric synthesis of the carbapenem antibiotic (+)-PS-5

Cited by 76 publications

References 0 publications

The S-Thioester Enolate/Imine Condensation: A Shortcut to β-Lactams

The S-Thioester Enolate/Imine Condensation: A Shortcut to β-Lactams

Copper‐catalyzed one‐pot synthesis of propargylamines via CH activation in PEG

Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis

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