'Diastereoselective Carbocyclization of 1,6-Heptadienes Triggered by Rhodium-Catalyzed Activation of an Olefinic C-H Bond'



Aissa, C ORCID: 0000-0003-0750-9435, Ho, KYT, Tetlow, DJ and Pin-No, M
(2014) 'Diastereoselective Carbocyclization of 1,6-Heptadienes Triggered by Rhodium-Catalyzed Activation of an Olefinic C-H Bond'. Angewandte Chemie International Edition, 53 (16). 4209 - 4212.

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Diastereoselective carbocyclization of 1,6-heptadienes triggered by rhodium-catalyzed activation of an olefinic C-H bond.pdf

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Abstract

The use of α,ω‐dienes as functionalization reagents for olefinic carbon–hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)‐catalyzed rearrangement of prochiral 1,6‐heptadienes into [2,2,1]‐cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium‐labeling studies and the isolation of a key intermediate are consistent with a group‐directed C-H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective.

Item Type: Article
Additional Information: ## TULIP Type: Articles/Papers (Journal) ##
Uncontrolled Keywords: C-H activation, diastereoselectivity, diene, rearrangement, rhodium
Depositing User: Symplectic Admin
Date Deposited: 19 Apr 2016 09:29
Last Modified: 13 Nov 2020 14:34
DOI: 10.1002/anie.201400080
Related URLs:
URI: http://livrepository.liverpool.ac.uk/id/eprint/3000629