Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes

Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes

A cobalt-diphosphine catalyst has been found to promote a formal [3 + 2] cycloaddition reaction between a cyclopropanol and an allene via cyclopropanol ring opening, which affords a 3-alkylidenecyclopentanol derivative with high regio- and diastereoselectivities. The reaction tolerates monosubstitut...

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Main Authors: Yang, Junfeng, Sun, Qiao, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Cobalt Catalysis
Cycloaddition
Online Access:https://hdl.handle.net/10356/151651
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1516512021-07-22T10:05:23Z Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes Yang, Junfeng Sun, Qiao Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Cobalt Catalysis Cycloaddition A cobalt-diphosphine catalyst has been found to promote a formal [3 + 2] cycloaddition reaction between a cyclopropanol and an allene via cyclopropanol ring opening, which affords a 3-alkylidenecyclopentanol derivative with high regio- and diastereoselectivities. The reaction tolerates monosubstituted, 1,1-disubstituted, and 1,3-disubstituted allenes and various functional groups. The reaction is proposed to proceed through carbometalation of the allene with a cobalt homoenolate followed by intramolecular carbonyl allylation of the resulting allylcobalt species. Ministry of Education (MOE) Nanyang Technological University This work was supported by the Ministry of Education (Singapore) and Nanyang Technological University (MOE2016-T2-2-043). 2021-07-22T10:05:23Z 2021-07-22T10:05:23Z 2019 Journal Article Yang, J., Sun, Q. & Yoshikai, N. (2019). Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes. ACS Catalysis, 9(3), 1973-1978. https://dx.doi.org/10.1021/acscatal.8b05114 2155-5435 0000-0002-8997-3268 https://hdl.handle.net/10356/151651 10.1021/acscatal.8b05114 2-s2.0-85061547704 3 9 1973 1978 en MOE2016-T2-2-043 ACS Catalysis © 2019 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Cobalt Catalysis
Cycloaddition
spellingShingle Science::Chemistry
Cobalt Catalysis
Cycloaddition
Yang, Junfeng
Sun, Qiao
Yoshikai, Naohiko
Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
description A cobalt-diphosphine catalyst has been found to promote a formal [3 + 2] cycloaddition reaction between a cyclopropanol and an allene via cyclopropanol ring opening, which affords a 3-alkylidenecyclopentanol derivative with high regio- and diastereoselectivities. The reaction tolerates monosubstituted, 1,1-disubstituted, and 1,3-disubstituted allenes and various functional groups. The reaction is proposed to proceed through carbometalation of the allene with a cobalt homoenolate followed by intramolecular carbonyl allylation of the resulting allylcobalt species.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Yang, Junfeng
Sun, Qiao
Yoshikai, Naohiko
format Article
author Yang, Junfeng
Sun, Qiao
Yoshikai, Naohiko
author_sort Yang, Junfeng
title Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
title_short Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
title_full Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
title_fullStr Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
title_full_unstemmed Cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
title_sort cobalt-catalyzed regio- and diastereoselective formal [3 + 2] cycloaddition between cyclopropanols and allenes
publishDate 2021
url https://hdl.handle.net/10356/151651
_version_ 1707050428377595904

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