Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes

Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes

A cobalt–chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment sugg...

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Main Authors: Lee, Pin-Sheng, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/106746
http://hdl.handle.net/10220/25067
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1067462023-02-28T19:45:07Z Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes Lee, Pin-Sheng Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry A cobalt–chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C–C reductive elimination steps. Accepted version 2015-02-16T08:19:22Z 2019-12-06T22:17:30Z 2015-02-16T08:19:22Z 2019-12-06T22:17:30Z 2014 2014 Journal Article Lee, P.-S., & Yoshikai, N. (2015). Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes. Organic letters, 17(1), 22-25. 1523-7060 https://hdl.handle.net/10356/106746 http://hdl.handle.net/10220/25067 10.1021/ol503119z en Organic letters © 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Letters, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/ol503119z]. 6 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Lee, Pin-Sheng
Yoshikai, Naohiko
Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
description A cobalt–chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C–C reductive elimination steps.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Lee, Pin-Sheng
Yoshikai, Naohiko
format Article
author Lee, Pin-Sheng
Yoshikai, Naohiko
author_sort Lee, Pin-Sheng
title Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
title_short Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
title_full Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
title_fullStr Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
title_full_unstemmed Cobalt-catalyzed enantioselective directed C-H alkylation of indole with styrenes
title_sort cobalt-catalyzed enantioselective directed c-h alkylation of indole with styrenes
publishDate 2015
url https://hdl.handle.net/10356/106746
http://hdl.handle.net/10220/25067
_version_ 1759854703438462976

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