Diastereoselective Syntheses of (3R*,4R*)- and (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues
Diastereoselective Syntheses of (3R*,4R*)- and (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues
Two concise and high-yielding diastereoselective syntheses of 4-aryl-3-methyl-4-piperidinemethanols were realized from 1,3-dimethyl-4-piperidinone. The key reactions to control the C3–C4 relative stereochemistry were the alkoxymethylation of a metalloenamine generated from 4-aryl-3-methyl-1,2,3,6-tetrahydropyridine that afforded the (3R*,4S*)-form and the nucleophilic substitution of a fluoroarene with deprotonated 3-methyl-4-piperidinenitrile giving the (3R*,4R*)-isomer. The corresponding fluoromethyl analogues were subsequently obtained through the fluorination of the piperidinemethanols using DAST.
1222-1229
Schmitt, Sébastien
7f3b6436-dc43-4651-8490-317337271260
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Perrio, Cécile
2155a2f3-6a4f-423a-aa40-07f56506f2df
1 February 2013
Schmitt, Sébastien
7f3b6436-dc43-4651-8490-317337271260
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Perrio, Cécile
2155a2f3-6a4f-423a-aa40-07f56506f2df
Schmitt, Sébastien, Brown, Richard C. D. and Perrio, Cécile
(2013)
Diastereoselective Syntheses of (3R*,4R*)- and (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues.
Journal of Organic Chemistry, 78 (3), .
(doi:10.1021/Jo302303h).
Abstract
Two concise and high-yielding diastereoselective syntheses of 4-aryl-3-methyl-4-piperidinemethanols were realized from 1,3-dimethyl-4-piperidinone. The key reactions to control the C3–C4 relative stereochemistry were the alkoxymethylation of a metalloenamine generated from 4-aryl-3-methyl-1,2,3,6-tetrahydropyridine that afforded the (3R*,4S*)-form and the nucleophilic substitution of a fluoroarene with deprotonated 3-methyl-4-piperidinenitrile giving the (3R*,4R*)-isomer. The corresponding fluoromethyl analogues were subsequently obtained through the fluorination of the piperidinemethanols using DAST.
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e-pub ahead of print date: 8 January 2013
Published date: 1 February 2013
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 356408
URI: http://eprints.soton.ac.uk/id/eprint/356408
ISSN: 0022-3263
PURE UUID: d549fb9f-a675-430c-9854-bb0f5981d94f
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Date deposited: 02 Oct 2013 14:25
Last modified: 15 Mar 2024 02:53
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Author:
Sébastien Schmitt
Author:
Cécile Perrio
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