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Atroposelective Synthesis of PINAP via Dynamic Kinetic Asymmetric Transformation

Han, Seo-Jung and Bhat, Vikram and Stoltz, Brian M. and Virgil, Scott C. (2019) Atroposelective Synthesis of PINAP via Dynamic Kinetic Asymmetric Transformation. Advanced Synthesis and Catalysis, 361 (3). pp. 441-444. ISSN 1615-4150. https://resolver.caltech.edu/CaltechAUTHORS:20181113-112609134

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Abstract

The atroposelective synthesis of PINAP ligands has been accomplished via a palladium‐catalyzed C−P coupling process through dynamic kinetic asymmetric transformation. These catalytic conditions allow access to a wide variety of alkoxy‐ and benzyloxy‐substituted PINAP ligands in high enantiomeric excess. The methods described in this communication afford valuable P,N ligands in good yields and high enantioselectivity using low catalyst loading.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/adsc.201801248DOIArticle
ORCID:
AuthorORCID
Bhat, Vikram0000-0001-5621-5121
Stoltz, Brian M.0000-0001-9837-1528
Virgil, Scott C.0000-0001-8586-5641
Additional Information:© 2018 WILEY‐VCH Verlag. Issue Online: 01 February 2019; Version of Record online: 07 December 2018; Accepted manuscript online: 08 November 2018; Manuscript revised: 08 November 2018; Manuscript received: 18 September 2018. The authors wish to thank NIH‐NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. S.‐J.H. thanks the Fulbright program (Foreign Student Program, No. 15111120), the Ilju Foundation of Education & Culture (Pre‐doctoral Research Fellowship), and the KIST institutional program (2E28570, 2E28010) for financial support.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Caltech Center for Catalysis and Chemical SynthesisUNSPECIFIED
Fulbright Foundation15111120
Ilju Foundation of Education & CultureUNSPECIFIED
Korea Institute of Science and Technology (KIST)2E28570
Korea Institute of Science and Technology (KIST)2E28010
Subject Keywords:PINAP; Dynamic kinetic asymmetric transformation; Atroposelective synthesis; P,N ligands
Issue or Number:3
Record Number:CaltechAUTHORS:20181113-112609134
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20181113-112609134
Official Citation:S.-J. Han, V. Bhat, B. M. Stoltz, S. C. Virgil, Adv. Synth. Catal. 2019, 361, 441. doi: 10.1002/adsc.201801248
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:90863
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:14 Nov 2018 15:36
Last Modified:09 Mar 2020 13:19

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