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Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

Daniels, Blake E. and Ni, Jane and Reisman, Sarah E. (2016) Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction. Angewandte Chemie International Edition, 55 (10). pp. 3398-3402. ISSN 1433-7851. PMCID PMC4843768. doi:10.1002/anie.201510972. https://resolver.caltech.edu/CaltechAUTHORS:20160208-143917247

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Abstract

A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl_4 and 3,3′-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl_4⋅BINOL complex serves as a chiral Lewis-acid-assisted Brønsted acid.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201510972DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4843768/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2016 John Wiley & Sons, Inc. Received: November 26, 2015. Published online: February 4, 2016. Funded by: National Institutes of Health. Grant Number: RR027690; NSERC; American Cancer Society Research Scholar; NIH, Grant Number: RGM097582A; American Chemical Society PRF.
Funders:
Funding AgencyGrant Number
NIHRR027690
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
American Cancer SocietyUNSPECIFIED
NIHRGM097582A
American Chemical Society Petroleum Research FundUNSPECIFIED
Subject Keywords:Cyclisierungen; Enantioselektivität; Heterocyclen; Lewis-Säuren; Zirconium
Issue or Number:10
PubMed Central ID:PMC4843768
DOI:10.1002/anie.201510972
Record Number:CaltechAUTHORS:20160208-143917247
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160208-143917247
Official Citation:B. E. Daniels, J. Ni, S. E. Reisman, Angew. Chem. Int. Ed. 2016, 55, 3398. Angew. Chem.. doi:10.1002/ange.201510972
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64312
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:08 Feb 2016 23:05
Last Modified:10 May 2022 19:41

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