2017
DOI: 10.1002/chem.201701944
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β‐Hydroxy‐tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE‐412

Abstract: A new synthetic protocol provides a simple and direct method to generate functionalized β-hydroxy-tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation led to the formation of functionalized β-hydroxy-tetrahydroquinolines. High regio and diastereoselectivities were observed in α or γ substituted quinolines and the trans diastereomer of β-hydroxy-THQ was the major isostere. This new protocol was utilized to build the novel antibody-targeted lupus peptidomimetic FISLE… Show more

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Cited by 9 publications
(8 citation statements)
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“…For example, in situ generated metal hydride species based on Mg, Rh, Zn, La, and Th were found to promote 1,2‐hydroboration of pyridines while 1,4‐selectivity was observed via an ionic outer‐sphere pathway catalysed by Lewis or Brønsted acids . Despite these recent advances in the dearomative hydroboration of N ‐heteroarenes, to our best knowledge, no catalytic procedures have been revealed thus far for the sp 3 C−B bond‐forming hydroboration of N ‐heteroaromatics …”
Section: Methodsmentioning
confidence: 99%
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“…For example, in situ generated metal hydride species based on Mg, Rh, Zn, La, and Th were found to promote 1,2‐hydroboration of pyridines while 1,4‐selectivity was observed via an ionic outer‐sphere pathway catalysed by Lewis or Brønsted acids . Despite these recent advances in the dearomative hydroboration of N ‐heteroarenes, to our best knowledge, no catalytic procedures have been revealed thus far for the sp 3 C−B bond‐forming hydroboration of N ‐heteroaromatics …”
Section: Methodsmentioning
confidence: 99%
“…Indeed, our group recently reported the B(C 6 F 5 ) 3catalyzed silylative reduction of pyridines, quinolines, and α,β-unsaturated nitriles and imines to afford C (sp 3 )À Si moiety-containing products (Scheme 1b). [7] Herein we report a B(C 6 F 5 ) 3 -catalyzed double hydroboration of quinolines to give rise to β-borylated tetrahydroquinolines (Scheme 1d). [6] For example, in situ generated metal hydride species based on Mg, Rh, Zn, La, and Th were found to promote 1,2-hydroboration of pyridines [6a-f] while 1,4-selectivity was observed via an ionic outersphere pathway catalysed by Lewis or Brønsted acids.…”
mentioning
confidence: 99%
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“…The peptides' small molecular property has advantages in high-throughput and standardized synthesis technology. A practical, simplified synthetic method has been attempted to achieve rapid and cheap synthesis [106]. FISLE-412 was well tolerated and had no toxicity nor immunogenicity [105].…”
Section: Fisle-412mentioning
confidence: 99%