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The asymmetric aza-silyl-Prins reaction: synthesis of enantiopure piperidines

The asymmetric aza-silyl-Prins reaction: synthesis of enantiopure piperidines
The asymmetric aza-silyl-Prins reaction: synthesis of enantiopure piperidines
The design and development of the first asymmetric aza-silyl-Prins reaction is reported, giving rise to valuable and diverse piperidines and pipecolic acid derivatives in both high yields and as single enantiomers. The creation of a novel chiral auxiliary-homoallylic amine for the aza-silylPrins reaction is essential to its success.
1523-7060
350-355
Mittapalli, Ramana R.
8579d1b9-5d0c-46ae-95b9-22f022aff90a
Guesné, Sebastien J.J.
5c746d98-0c89-499d-927f-014e8af83b28
Parker, Robert J.
a3a6bf55-8309-426f-8621-a28599edb476
Klooster, Wim
64dc0111-f415-4226-9189-45764c0933d9
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Skidmore, John
53f63731-e26e-484e-a901-701415aa5066
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54
Mittapalli, Ramana R.
8579d1b9-5d0c-46ae-95b9-22f022aff90a
Guesné, Sebastien J.J.
5c746d98-0c89-499d-927f-014e8af83b28
Parker, Robert J.
a3a6bf55-8309-426f-8621-a28599edb476
Klooster, Wim
64dc0111-f415-4226-9189-45764c0933d9
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Skidmore, John
53f63731-e26e-484e-a901-701415aa5066
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54

Mittapalli, Ramana R., Guesné, Sebastien J.J., Parker, Robert J., Klooster, Wim, Coles, Simon J., Skidmore, John and Dobbs, Adrian P. (2018) The asymmetric aza-silyl-Prins reaction: synthesis of enantiopure piperidines. Organic Letters, 21 (2), 350-355. (doi:10.1021/acs.orglett.8b03283).

Record type: Article

Abstract

The design and development of the first asymmetric aza-silyl-Prins reaction is reported, giving rise to valuable and diverse piperidines and pipecolic acid derivatives in both high yields and as single enantiomers. The creation of a novel chiral auxiliary-homoallylic amine for the aza-silylPrins reaction is essential to its success.

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Accepted/In Press date: 18 December 2018
e-pub ahead of print date: 28 December 2018
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Identifiers

Local EPrints ID: 427590
URI: http://eprints.soton.ac.uk/id/eprint/427590
DOI: doi:10.1021/acs.orglett.8b03283
ISSN: 1523-7060
PURE UUID: bc86a244-c2d6-4427-bbd1-3cc08d044411
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 23 Jan 2019 17:30
Last modified: 16 Mar 2024 07:30

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Contributors

Author: Ramana R. Mittapalli
Author: Sebastien J.J. Guesné
Author: Robert J. Parker
Author: Wim Klooster
Author: Simon J. Coles ORCID iD
Author: John Skidmore
Author: Adrian P. Dobbs

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