PMID: 11902878Mar 21, 2002Paper

Dynamic kinetic resolution via asymmetric conjugate reduction: enantio- and diastereoselective synthesis of 2,4-dialkyl cyclopentanones

Journal of the American Chemical Society
Valdas Jurkauskas, Stephen L Buchwald

Abstract

Herein, we report the kinetic and the dynamic kinetic resolutions of racemic 3,5-dialkyl-2-cyclopenten-1-ones. Kinetic resolution, with good selectivity factors (25-52), was achieved by conjugate reduction with catalytic CuCl/NaOt-Bu/(S)-p-tol-BINAP and stoichiometric quantities of poly(methylhydrosiloxane) (PMHS). When stoichiometric amounts of NaOt-Bu and t-BuOH were included in the reaction mixture, rapid racemization of the starting material occurred allowing for the dynamic kinetic resolution of the cyclopentenone substrates. In this process, chiral 2,4-dialkylcyclopentanones were isolated with high stereoselectivity (ee > or = 91%, dr > or = 90:10) and in high yield (> or =89%).

Citations

Feb 15, 2007·Organic Letters·Kenneth A Miller, Stephen F Martin
Apr 7, 2004·Proceedings of the National Academy of Sciences of the United States of America·Matthew P RainkaStephen L Buchwald
Apr 22, 2016·Chemical Reviews·Svilen P SimeonovCarlos A M Afonso
Jun 3, 2017·Journal of the American Chemical Society·Amy A OttJoseph J Topczewski
Dec 21, 2004·Organic Letters·Junghyun ChaeStephen L Buchwald
Dec 18, 2014·Nature Chemistry·Shi-Liang Shi, Stephen L Buchwald
Jun 9, 2005·Angewandte Chemie·Edwin Vedejs, Mara Jure
Feb 12, 2019·Angewandte Chemie·Zhiwei ChenVy M Dong
Dec 15, 2015·Angewandte Chemie·Michael T PirnotStephen L Buchwald
Jul 21, 2011·Organic & Biomolecular Chemistry·Ninglin LiPauline Chiu
Feb 23, 2020·Chemistry : a European Journal·Mark A MaskeriKarl A Scheidt
Feb 4, 2021·Accounts of Chemical Research·Ryan T DavisonVy M Dong
Dec 10, 2009·Journal of the American Chemical Society·Bai-Lin LeiXue-Long Hou
Dec 9, 2009·Organic Letters·Andrew D Kosal, Brandon L Ashfeld
Jul 12, 2008·Chemical Reviews·Carl Deutsch, Norbert Krause
Nov 6, 2018·Organic Letters·Amy A Ott, Joseph J Topczewski
Oct 11, 2013·Journal of the American Chemical Society·Shaolin ZhuStephen L Buchwald
Oct 14, 2005·Journal of the American Chemical Society·Gregory HughesStephen L Buchwald
Oct 13, 2021·Organic Letters·Xiang Ren, Zhan Lu

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