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A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters

Schmidt, Jens and Choi, Junwon and Liu, Albert Tianxiang and Slusarczyk, Martin and Fu, Gregory C. (2016) A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters. Science, 354 (6317). pp. 1265-1269. ISSN 0036-8075. PMCID PMC5619240. doi:10.1126/science.aai8611.

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Alkylboron compounds are an important family of target molecules, serving as useful intermediates, as well as end points, in fields such as pharmaceutical science and organic chemistry. Facile transformation of carbon-boron bonds into a wide variety of carbon-X bonds (where X is, for example, carbon, nitrogen, oxygen, or a halogen), with stereochemical fidelity, renders the generation of enantioenriched alkylboronate esters a powerful tool in synthesis. Here we report the use of a chiral nickel catalyst to achieve stereoconvergent alkyl-alkyl couplings of readily available racemic α-haloboronates with organozinc reagents under mild conditions. We demonstrate that this method provides straightforward access to a diverse array of enantioenriched alkylboronate esters, in which boron is bound to a stereogenic carbon, and we highlight the utility of these compounds in synthesis.

Item Type:Article
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URLURL TypeDescription Materials CentralArticle
Choi, Junwon0000-0001-6004-5524
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2016 American Association for the Advancement of Science. 23 August 2016; accepted 3 November 2016. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, R01-GM62871), the Alexander von Humboldt Foundation (fellowship for J.S.), the German National Merit Foundation (fellowship for M.S.), the David S. Koons SURF (Summer Undergraduate Research Fellowship) Endowment (fellowship for A.T.L.), and the Gordon and Betty Moore Foundation (for the Caltech Center for Catalysis and Chemical Synthesis). We thank J. M. Ahn, L. M. Henling, M. K. Takase (Caltech X-Ray Crystallography Facility), N. D. Schley, M. Shahgholi (Caltech Mass Spectrometry Facility), D. G. VanderVelde (Caltech NMR Facility), and S. C. Virgil (Caltech Center for Catalysis and Chemical Synthesis) for assistance and helpful discussions. Experimental procedures and characterization data are provided in the supplementary materials. Crystallographic data are available free of charge from the Cambridge Crystallographic Data Centre under reference CCDC-1512445.
Funding AgencyGrant Number
Alexander von Humboldt FoundationUNSPECIFIED
Studienstiftung des deutschen VolkesUNSPECIFIED
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Issue or Number:6317
PubMed Central ID:PMC5619240
Record Number:CaltechAUTHORS:20161212-113915733
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Official Citation:A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters BY JENS SCHMIDT, JUNWON CHOI, ALBERT TIANXIANG LIU, MARTIN SLUSARCZYK, GREGORY C. FU Science 09 Dec 2016: Vol. 354, Issue 6317, pp. 1265-1269 DOI: 10.1126/science.aai8611
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:72724
Deposited By: George Porter
Deposited On:12 Dec 2016 21:42
Last Modified:07 Apr 2022 16:09

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