2011
DOI: 10.1021/ol103050c
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Synthesis of Novel Angular Spirocyclic Azetidines

Abstract: The syntheses of a variety of novel angular azaspiro[3.3]heptanes are reported. gem-Difluoro and gem-dimethyl variants of the angular 1,6-diazaspiro[3.3]heptane module were prepared in high yields using efficient sequences. Additionally, a practical one-pot synthesis of 5-oxo-2-azaspiro[3.3]heptanes and subsequent conversions into functionalized derivatives are described. The methods reported are amenable to the synthesis of these building blocks for drug discovery as members of a library or individually on a … Show more

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Cited by 66 publications
(34 citation statements)
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“…Simple azetidines partook the reaction to give 2a-c while azaspiro [3,3]heptane analogues were unreactive. The higher reactivity of azaspiro [3,4]octane example 3d highlights the distinct reactivity of azaspiro [3,3]heptanes. On one hand, a rationalization of this observation could be traced back to the first step of the catalytic cycle.…”
Section: Resultsmentioning
confidence: 99%
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“…Simple azetidines partook the reaction to give 2a-c while azaspiro [3,3]heptane analogues were unreactive. The higher reactivity of azaspiro [3,4]octane example 3d highlights the distinct reactivity of azaspiro [3,3]heptanes. On one hand, a rationalization of this observation could be traced back to the first step of the catalytic cycle.…”
Section: Resultsmentioning
confidence: 99%
“…Reduction of the nickel(II) pre-catalyst to nickel(0) is believed to occur by β-hydride elimination on a sacrificial amount of amine [10]. The strained character of azaspiro [3,3]heptane might prevent this event. On the other hand, pyramidalization at nitrogen is much more important in azetidines [16][17][18].…”
Section: Resultsmentioning
confidence: 99%
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“…The power of this method is demonstrated by a concise formal total synthesis of racemic cephalotaxine. It is worth mentioning that this method has found applications in the synthesis of azacycles35 and alkaloid FR901483 ( 1 ) 18b…”
Section: Resultsmentioning
confidence: 99%