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Issue 51, 2017
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Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(ii)–SPRIX-catalyzed C–H activation

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Abstract

The highly enantioselective cyclization of 3-alkenylindole via C–H activation has been established using Pd(OCOCF3)2 in conjunction with the chiral spiro bis(isoxazoline) ligand (SPRIX). The presence of an N-allyl substituent on the substrate has a strong impact on both reactivity and selectivity, leading to tricyclic indole products (up to 96% ee) with a chiral quaternary carbon center.

Graphical abstract: Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(ii)–SPRIX-catalyzed C–H activation

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Article information


Submitted
25 Apr 2017
Accepted
06 Jun 2017
First published
06 Jun 2017

Chem. Commun., 2017,53, 6887-6890
Article type
Communication

Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(II)–SPRIX-catalyzed C–H activation

M. A. Abozeid, S. Sairenji, S. Takizawa, M. Fujita and H. Sasai, Chem. Commun., 2017, 53, 6887
DOI: 10.1039/C7CC03199H

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