Development of a Stepwise [3 + 3] Annelation to Functionalized Piperidines

Goodenough, Katharine M.; Raubo, Piotr; Harrity, Joseph P. A.

doi:10.1021/ol050965t

Cited by 45 publications

(11 citation statements)

References 13 publications

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“…This method was proposed to proceed via the Pd(p-allyl) intermediate but it consumed high catalyst loading [Pd(OAc) 2 -10 mol% and PPh 3 -40 mol%] together with 25 mol% of Ti(OiPr) 4 (Scheme 29). 40 2.2.6 Other allylic alcohol activation processes. The [Pd(0)-SnCl 2 ]catalytic system has shown a good applicability for allylation of amines with various allylic alcohols.…”

Section: Activation Of Alcohols In the Presence Of Boron Additivesmentioning

confidence: 99%

Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species

2012

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Modern organic synthesis now requires efficient atom economical synthetic methods operating under greener pathways to achieve C-C and C-heteroatom bond formation. Direct activation of allylic alcohols in the presence of transition metal catalysts leading to electrophilic π-allyl metal intermediates represents such a promising target in the field of nucleophilic allylation reactions. During the last decade, this topic of recognized importance has become an emerging area, and selected transition metals, sometimes associated with alcohol activators, have brought elegant solutions for performing allylic substitution directly from alcohols in a regio, stereo and enantioselective manner.

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Section: Activation Of Alcohols In the Presence Of Boron Additivesmentioning

confidence: 99%

Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species

2012

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“…In this approach, stepwise Grignard addition-cyclization of aziridines 376 with allyl alcohol derivative 377 furnished the piperidines 379 in good yields with broader substrate scope (Scheme 96) [165]. The newly developed synthetic strategy was successfully applied for the formal synthesis of (AE)-perhydrohistrionicotoxin [166].…”

Section: Synthesis Of Six-membered Rings From Activated Aziridines Anmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

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“…Intramolecular palladium-catalyzed N-allylations of amino-tethered allylic alcohols to give 3-methylene-piperidines were reported (Eq. (91)) [676]. An interesting palladium-catalyzed aziridine ring-opening intramolecular amination reaction was examined as an approach toward nufar alkaloids [677].…”

Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Development of a Stepwise [3 + 3] Annelation to Functionalized Piperidines

Abstract: [reaction: see text] A stepwise formal [3 + 3] cycloaddition sequence via a Grignard addition-cyclization reaction leads to a much improved piperidine synthesis. This methodology provides improved flexibility in both the aziridine substrate and TMM equivalent.

Cited by 45 publications

References 13 publications

Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species

Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species

Ring Expansions of Activated Aziridines and Azetidines

Transition metals in organic synthesis: Highlights for the year 2005

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