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Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers

Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers
Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers
The solid-phase synthesis of 4-methylene pyrrolidines and allylic amines has been achieved using palladium-catalysed nucleophilic cleavage of allylic linkages. Six pyrrolidines were synthesised in five steps from a carboxyethyl resin 20, where the key transformations included a Lewis-acid promoted imino-Sakurai type reaction and reductive alkylation prior to the final palladium-catalysed cyclisation cleavage of the allylic carboxylate linkage. Allylic carboxylate resin 22 was also shown to undergo "traceless" cleavage using various hydride sources in the presence of catalytic palladium. A more robust allylic ether linkage was also investigated. Starting from a phenol resin 36, a number of 3-aryl-allylamines were prepared using a palladium-catalysed nucleophilic cleavage reaction.
organic-synthesis, combinatorial chemistry, drug discovery, mitsunobu reaction, traceless linkers, protecting groups, resin, strategies, cleavage, libraries
1477-0520
2699-2709
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Fisher, Martyn L.
22c843f0-48a2-4632-a0b5-0a5747511504
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Fisher, Martyn L.
22c843f0-48a2-4632-a0b5-0a5747511504
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b

Brown, Richard C.D., Fisher, Martyn L. and Brown, Lynda J. (2003) Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers. Organic & Biomolecular Chemistry, 1 (15), 2699-2709. (doi:10.1039/b303752e). (PMID:12948194)

Record type: Article

Abstract

The solid-phase synthesis of 4-methylene pyrrolidines and allylic amines has been achieved using palladium-catalysed nucleophilic cleavage of allylic linkages. Six pyrrolidines were synthesised in five steps from a carboxyethyl resin 20, where the key transformations included a Lewis-acid promoted imino-Sakurai type reaction and reductive alkylation prior to the final palladium-catalysed cyclisation cleavage of the allylic carboxylate linkage. Allylic carboxylate resin 22 was also shown to undergo "traceless" cleavage using various hydride sources in the presence of catalytic palladium. A more robust allylic ether linkage was also investigated. Starting from a phenol resin 36, a number of 3-aryl-allylamines were prepared using a palladium-catalysed nucleophilic cleavage reaction.

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More information

Published date: 2003
Keywords: organic-synthesis, combinatorial chemistry, drug discovery, mitsunobu reaction, traceless linkers, protecting groups, resin, strategies, cleavage, libraries

Identifiers

Local EPrints ID: 19916
URI: https://eprints.soton.ac.uk/id/eprint/19916
ISSN: 1477-0520
PURE UUID: fc61acae-0b1d-4ff0-84d1-bdb4baf78265
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814

Catalogue record

Date deposited: 23 Feb 2006
Last modified: 20 Jul 2019 01:16

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