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Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines

Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines
Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines
How to close a ring: An approach to catalytic asymmetric 6? electrocyclization leads to a highly enantioselective process that was used in the synthesis of chiral indolines (see scheme). Treatment of N-aryl imines under phase transfer conditions in the presence of N-benzyl cinchonidinium chloride generates a delocalized 2-aza-pentadienyl anion system that cyclizes in up to 99?% yield and 98?%?ee.
1433-7851
9979-9982
Maciver, Eleanor E.
caf4abe2-7e52-419f-ba64-b4248f7d4024
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Smith, Martin D.
871dbd2f-83bb-4c7e-ab1d-c890394db215
Maciver, Eleanor E.
caf4abe2-7e52-419f-ba64-b4248f7d4024
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Smith, Martin D.
871dbd2f-83bb-4c7e-ab1d-c890394db215

Maciver, Eleanor E., Thompson, Sam and Smith, Martin D. (2009) Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines. Angewandte Chemie International Edition, 48 (52), 9979-9982. (doi:10.1002/anie.200905169).

Record type: Article

Abstract

How to close a ring: An approach to catalytic asymmetric 6? electrocyclization leads to a highly enantioselective process that was used in the synthesis of chiral indolines (see scheme). Treatment of N-aryl imines under phase transfer conditions in the presence of N-benzyl cinchonidinium chloride generates a delocalized 2-aza-pentadienyl anion system that cyclizes in up to 99?% yield and 98?%?ee.

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e-pub ahead of print date: 4 November 2009
Published date: 21 December 2009
Organisations: Chemistry

Identifiers

Local EPrints ID: 403613
URI: http://eprints.soton.ac.uk/id/eprint/403613
ISSN: 1433-7851
PURE UUID: 20231832-1827-4fc4-83b9-8419186c0694
ORCID for Sam Thompson: ORCID iD orcid.org/0000-0001-6267-5693

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Date deposited: 07 Dec 2016 13:38
Last modified: 03 Dec 2019 01:32

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