2017
DOI: 10.1016/bs.aihch.2016.10.002
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of Piperidines and Dehydropiperidines

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
4
1

Citation Types

0
11
0

Year Published

2018
2018
2023
2023

Publication Types

Select...
8

Relationship

0
8

Authors

Journals

citations
Cited by 27 publications
(11 citation statements)
references
References 228 publications
0
11
0
Order By: Relevance
“…Therefore we prepared mono-( 8) 32 and di-phenyl ( 7) [33][34] allylmorpholin-2-ones in both enantiomeric forms in just 4 steps, as two new chiral platforms containing a homoallylic amine. Following the rationale presented in Scheme 1 (2), the phenyl substituents were chosen as these would both facilitate rapid removal of part of the chiral platform post Prins cyclisation and crucially block one face from anion trapping. Treatment of either (7) or (8) with NaHMDS and an allyl or propargylic bromide gave a small library of enantiomerically pure secondary amines (Table 1).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Therefore we prepared mono-( 8) 32 and di-phenyl ( 7) [33][34] allylmorpholin-2-ones in both enantiomeric forms in just 4 steps, as two new chiral platforms containing a homoallylic amine. Following the rationale presented in Scheme 1 (2), the phenyl substituents were chosen as these would both facilitate rapid removal of part of the chiral platform post Prins cyclisation and crucially block one face from anion trapping. Treatment of either (7) or (8) with NaHMDS and an allyl or propargylic bromide gave a small library of enantiomerically pure secondary amines (Table 1).…”
Section: Resultsmentioning
confidence: 99%
“…The vast majority of these drugs require careful stereocontrol of the substitutents around the ring during manufacture. Methods for their synthesis have been widely reviewed [2][3][4][5] but the greatest problem has always been the asymmetric construction of the piperidine ring. Furthermore, there is an emerging need for sp 3 -rich heterocyclic frameworks, again with both relative and absolute stereocontrol of the substituents.…”
Section: Introductionmentioning
confidence: 99%
“…10 Indeed, sterically challenged 1b failed to react even at elevated temperatures (up to 150 C) even though constitutionally isomeric 2,2-dimethylglutaric anhydride reacted efficiently with 1,3-azadienes of type 2 at 110 C. 10 In the current study, we seek to evaluate the performance (with respect to reactivity, diastereoselectivity, and chemoselectivity) of 3-methylglutaric anhydride (1c) toward 1,3-azadiene partners, and elaborate the product (i.e., 3c) to several synthetically and pharmaceutically attractive topologies (see 4-7). Since many existing cyclization strategies for piperidine synthesis tend to exhibit poor generality, suffer from low regio-and stereochemical control, require protecting group manipulations, or depend on a specic directing group, 11 we anticipate that the current approach, which side-steps these aforementioned limitations, would greatly expand the structural space for the discovery of new piperidine pharmacophores. Indeed, this anhydride-imine reaction is known to be a powerful tool for the synthesis of combinatorial and targeted compound libraries as well as for producing building blocks in multigram (up to 100 g) scale.…”
Section: Introductionmentioning
confidence: 99%
“…, 3c) to several synthetically and pharmaceutically attractive topologies (see 4–7). Since many existing cyclization strategies for piperidine synthesis tend to exhibit poor generality, suffer from low regio- and stereochemical control, require protecting group manipulations, or depend on a specific directing group, 11 we anticipate that the current approach, which side-steps these aforementioned limitations, would greatly expand the structural space for the discovery of new piperidine pharmacophores. Indeed, this anhydride-imine reaction is known to be a powerful tool for the synthesis of combinatorial and targeted compound libraries as well as for producing building blocks in multigram (up to 100 g) scale.…”
Section: Introductionmentioning
confidence: 99%
“…4 Moreover, the number of enantioselective approaches that allow a one-step access to these scaffolds is rather limited. 5 These drawbacks are even more pronounced in the case of piperidines containing highly substituted carbon stereocenters adjacent to their nitrogen atom. 6 The piperidine scaffold is also embedded in the skeleton of many polycyclic natural products exhibiting complex structures.…”
Section: Introductionmentioning
confidence: 99%