On the scope of Pd-catalyzed carboamination reactions - synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines

Tue Heesgaard Jepsen; Mogens Larsen; Mogens Brøndsted Nielsen

On the scope of Pd-catalyzed carboamination reactions - synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines

Tue Heesgaard Jepsen, Mogens Larsen, Mogens Brøndsted Nielsen

Department of Chemistry

7 Citations (Scopus)

Abstract

The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated. Formation of a 2,4-disubstituted pyrrolidine proceeded in high yield but with a diastereoisomeric ratio of only 2:5, favoring the cis-isomer. The diastereoselectivity is hence significantly smaller than that observed previously in the formation of 2,3- and 2,5-disubstituted pyrrolidines. The yields of substituted piperidines and morpholines were lowered by competing Heck arylation reactions. Both the N-substituent and the choice of phosphine ligand for the palladium-catalyzed reaction were determining for the outcome. The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated.

Original language	English
Journal	Tetrahedron
Volume	66
Issue number	32
Pages (from-to)	6133-6137
ISSN	0040-4020
Publication status	Published - 7 Aug 2010

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title = "On the scope of Pd-catalyzed carboamination reactions - synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines",

abstract = "The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated. Formation of a 2,4-disubstituted pyrrolidine proceeded in high yield but with a diastereoisomeric ratio of only 2:5, favoring the cis-isomer. The diastereoselectivity is hence significantly smaller than that observed previously in the formation of 2,3- and 2,5-disubstituted pyrrolidines. The yields of substituted piperidines and morpholines were lowered by competing Heck arylation reactions. Both the N-substituent and the choice of phosphine ligand for the palladium-catalyzed reaction were determining for the outcome. The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated.",

author = "Jepsen, {Tue Heesgaard} and Mogens Larsen and Nielsen, {Mogens Br{\o}ndsted}",

year = "2010",

month = aug,

day = "7",

language = "English",

volume = "66",

pages = "6133--6137",

journal = "Tetrahedron",

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TY - JOUR

T1 - On the scope of Pd-catalyzed carboamination reactions - synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines

AU - Jepsen, Tue Heesgaard

AU - Larsen, Mogens

AU - Nielsen, Mogens Brøndsted

PY - 2010/8/7

Y1 - 2010/8/7

N2 - The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated. Formation of a 2,4-disubstituted pyrrolidine proceeded in high yield but with a diastereoisomeric ratio of only 2:5, favoring the cis-isomer. The diastereoselectivity is hence significantly smaller than that observed previously in the formation of 2,3- and 2,5-disubstituted pyrrolidines. The yields of substituted piperidines and morpholines were lowered by competing Heck arylation reactions. Both the N-substituent and the choice of phosphine ligand for the palladium-catalyzed reaction were determining for the outcome. The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated.

AB - The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated. Formation of a 2,4-disubstituted pyrrolidine proceeded in high yield but with a diastereoisomeric ratio of only 2:5, favoring the cis-isomer. The diastereoselectivity is hence significantly smaller than that observed previously in the formation of 2,3- and 2,5-disubstituted pyrrolidines. The yields of substituted piperidines and morpholines were lowered by competing Heck arylation reactions. Both the N-substituent and the choice of phosphine ligand for the palladium-catalyzed reaction were determining for the outcome. The scope of the palladium-catalyzed carboamination reaction for the synthesis of 2-substituted pyrrolidines, piperidines, and morpholines was investigated.

M3 - Journal article

SN - 0040-4020

VL - 66

SP - 6133

EP - 6137

JO - Tetrahedron

JF - Tetrahedron

IS - 32

ER -

On the scope of Pd-catalyzed carboamination reactions - synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines

Abstract

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