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Regioselectivity of Addition of Organolithium Reagents to Enones: The Role of HMPA - PubMed

. 1999 Jan 8;64(1):14-15.

doi: 10.1021/jo981765g.

Affiliations

Regioselectivity of Addition of Organolithium Reagents to Enones: The Role of HMPA

Hans J. Reich et al. J Org Chem. 1999.

No abstract available

The regioselectivity of addition of organolithium reagents to enones and enals: the role of HMPA.
Sikorski WH, Reich HJ. Sikorski WH, et al. J Am Chem Soc. 2001 Jul 11;123(27):6527-35. doi: 10.1021/ja010053w. J Am Chem Soc. 2001. PMID: 11439039
Substitution of a bridgehead bromide by primary organolithium reagents.
Harmata M, Wacharasindhu S. Harmata M, et al. Chem Commun (Camb). 2003 Oct 7;(19):2492-3. doi: 10.1039/b308112e. Chem Commun (Camb). 2003. PMID: 14587747
The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents.
Reich HJ, Sanders AW, Fiedler AT, Bevan MJ. Reich HJ, et al. J Am Chem Soc. 2002 Nov 13;124(45):13386-7. doi: 10.1021/ja026915q. J Am Chem Soc. 2002. PMID: 12418882
Hetero-aggregate compounds of aryl and alkyl lithium reagents: a structurally intriguing aspect of organolithium chemistry.
Gossage RA, Jastrzebski JT, van Koten G. Gossage RA, et al. Angew Chem Int Ed Engl. 2005 Feb 25;44(10):1448-54. doi: 10.1002/anie.200462103. Angew Chem Int Ed Engl. 2005. PMID: 15724254
Catalyst-controlled reverse selectivity in C-C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents.
Pizzolato SF, Giannerini M, Bos PH, Fañanás-Mastral M, Feringa BL. Pizzolato SF, et al. Chem Commun (Camb). 2015 May 11;51(38):8142-5. doi: 10.1039/c5cc01521a. Epub 2015 Apr 15. Chem Commun (Camb). 2015. PMID: 25872468

Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.
Lambert KM, Cox JB, Liu L, Jackson AC, Yruegas S, Wiberg KB, Wood JL. Lambert KM, et al. Angew Chem Int Ed Engl. 2020 Jun 8;59(24):9757-9766. doi: 10.1002/anie.202003829. Epub 2020 May 8. Angew Chem Int Ed Engl. 2020. PMID: 32271982 Free PMC article.
Breaking the tert-Butyllithium Contact Ion Pair: A Gateway to Alternate Selectivity in Lithiation Reactions.
Crockett MP, Piña J, Gogoi AR, Lalisse RF, Nguyen AV, Gutierrez O, Thomas AA. Crockett MP, et al. J Am Chem Soc. 2023 May 17;145(19):10743-10755. doi: 10.1021/jacs.2c13047. Epub 2023 May 3. J Am Chem Soc. 2023. PMID: 37133911 Free PMC article.