T. Howard Black a & Stephen L. Maluleka a a Department of Chemistry, Eastern Illinois
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1 This article was downloaded by: [University of Illinois] On: 18 July 2011, At: 16:50 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: Registered office: Mortimer House, Mortimer Street, London W1T 3JH, UK Synthetic Communications Publication details, including instructions for authors and subscription information: Isomerically Pure 2,3- Dialkyl 3-Alkenoic Acids via Ionization/Elimination of β- Lactones T. Howard Black a & Stephen L. Maluleka a a Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920, USA Available online: 24 Oct 2006 To cite this article: T. Howard Black & Stephen L. Maluleka (1989): Isomerically Pure 2,3-Dialkyl 3-Alkenoic Acids via Ionization/Elimination of β-lactones, Synthetic Communications, 19:16, To link to this article: PLEASE SCROLL DOWN FOR ARTICLE Full terms and conditions of use: terms-and-conditions This article may be used for research, teaching and private study purposes. Any substantial or systematic reproduction, re-distribution, reselling, loan, sub-licensing, systematic supply or distribution in any form to anyone is expressly forbidden. The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand or
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3 SYNTHETIC COMMUNICATIONS, 19(16), (1989) - m Q G W HM3 2,3+IATX& 3-AlXRU31C Iy3m6 VIA 1-rn-m OF B-IzcImEs T. Howard Black* and Stephen L. Maluleka of chemistry, Eastern Illinois University, Charles'tOn, Illinois, USA Abstract: 3-Substituted 4,4-didlkyl oxetan-2-ones undergo an idzation/elimination reaction to afford B,~-unsaturaW acid derivatives in high yield and isaneric pity. Unsaturated carboxylic - acids, especially those wherein the alkene brd is trisubstituted, play a major role in synthetic dwmistq, minq to their in several natural products (mist notably insect pheranones)' and their utility as synthetic intermediates.' A wide variety of strategies is available for the preparation of trisubstituted dlkene~,~ lxlt mist are incapatible with dired production of a cakqlic acid functianalit~.~ Additionally, although many methods are available for the preparation of conjugated W i c acids,5 acquisition of the corresponding A,Y isaners is considerably more difficult. 6 Wing an examination of &lactom rearrangements as amlied to problems of organic synthesis,7 we recently determined that spir0 B-lactones, when treated with Iewis acid catdlysts, rearrange to (I-cyclOdLkenyl) acetic acid derivatives.* It has 2885 Copyright by Marcel Dekker, Inc.
4 2886 BLACK AND MALULEKA now been determined that this chemistry works actmirably in acyclic cases, wherein the alkene borrls pmduced consist dusively of the wre hic$ily-substituted isaners. 'Ihus, w wish to report a sinple threestep method for the mnstruction of substituted B,yalkenoic acids, which requires minimdl plrification of intermediates and affords products mtzminated by amjqab3 isaners. 'Ihe synthetic sequen=e is depicted in the scheme, and yield data are collected in the Table. w=ze cons- via the amlensation of dilithicpxpanoic acid with a ketone (1) to pruvide the shydrcocy acid 2, which was then M ~ with W benzmfonyl chloride in pyrid.ine.lo mxmymmt was effected by treatment of 3 with magnesium brunide etherate in ether for six hrurs. 'Ihe appropriate &lactones 3 Geanetric prity and wz ratios were gaugd via EII%OII 125 m. In dll involving 2 - m -r~ me 9 NMR at (la+), elimination tmaxd the more highly-substituted carbon atan was the sole reactim pathway. ~ot surprisingly, when 3-dlkanones li and lj were exammed *, both possible dlkene isaners were obtained in each case (in essentially equal w o n ). The reaction also exhibits a mcdest stereoselectivity, in that the wz ratios in all cases w=ze approximately 2:1. 11 Earlier work has established that &lactones derive3 frun aldehydes (-, R'a) do not eliminate, but rather reamnge to tutyrolactones.u '~hus, the alkenoic acids are likely formed vi2 ionization of the &lactone follcxed by rapid loss of an adjacent
5 ISOMERICALLY PURE 2,3-DIALKYL 3-ALKENOIC ACIDS 2887 SCHEME 1 PhS&CI pyridina I+ Suffix R R a Me Me b Et Me C Me Et d Pr Me e Bu Me f Et Pr 9 CH Me 5 11 h Pr Bu i Pr Et j Bu Et 4 1 yiy Yielg Yiel$ of of 3 of e 77 f 90 a. Yields are uncptimized. b. All B-hydroxy acids viere oils which eliminated water upon attmpted distillation. c. Filtered thnxgh silica gel (dichloranethane eluent) prior to next step. d. All dlkenoic acids were oils which demrbxylated an attenpted distillation. e. misted of approximately equal amxlnts of indicated product and regioisaner (%Me, R =WI). f. misted of afpnorimately equal amxnts of indicated product ard regioisaner (I+?&, R =C+-I.,l).
6 2888 BLACK AND MALULEKA pmtm.!i% preference for isaners is likely due to energetic in the two carbaation rutamxi from which pmtm loss is likely. Obviously, 5 (whira W d lead to E prducts) is less qested than 6. That a higher stereoselectivity is not cbsemed is likely due to either a dep-ee of bond rotation prior to prvtan loss or insufficient steric hindrance in 6 (or a ambination). we are examining this aspect in greater detail. Pmpanoic acid dianion was used for this study to facilitate spectrdl interpretation; haever, s h other acetic acid derivatives have been successfully enplayed with cyclic ketnnes (e,g,, R,R'=(C35),),13 the current m&hd ShaiLd be similarly flexible. In I>'U~MIY, we have develcpd a general, highly stereaselective synthesis of 2,3-dialkyl 3-dlkerroic acids dmxacterized by ease of operatim, acoessibility of starting materials, ard high chemical and isaneric yield.
7 ISOMERICALLY PURE 2,3-DIALKYL 3-ALKENOIC ACIDS 2809 Ac)mxJl&d: we wish to thank the donors of the Wtmleum Research Fwd, administered by the American Qlaaicdl Society, along with the corporation, for support of this resear&. agh-field NMR data were aoquired with the assistance of the Molecular spectroscapy Iaboratory of the university of Illinois at Urbana-ign. 1. Mori, K. The Svnthes isofinsectfhermwxres,inthetatal svnthesis of Natural products. Vol. IV, ApsimOn, J., Ed.; Wiley- Interscience: New York, 1981; pp For exanple, see %mas, A.F. me Svnthesis of -, inmetatdlsvnth esis of Natural Produ cts, Vol. 11, ApSimOn, J., Ed.; Wiley-Interscience: New York, 1973; pp Naso, F. FWe -1. Umn. 1988, 60, A notable exception is ðyl arboxpethyl@ltxphom~; see Lmba?do, L.; Taylor, R.J.K. svnth. C~IDIUI. 1978, 8, For an exanple of a trisubsituted conjugated olefinic acid, see Miller, J.A.; Zwifel, G. J. Am. mem. Soc. 1981, 103, For exanples, see Oppolzer, W.; Icuendig, E.P.; BiSap, P.M.; Perret, C. Tetrahedron Lett. 1982, a, 3901 and SatO, T.; TaJexhi, M.; Itch, T.; Kawashima, M.; FUjisawa, T. ibid. 1981, - 22, a) Black, T.H.; Ix1Bay, W.J. TetratAmn Iiett. 1987, a, b) Black, T.H.; Hall, J.A.; Sheu, R.G. J. Om. mem. 1988,
8 2890 BLACK AND MALULEKA - 53, c) Black, T.H.; tn3ay, W.J. 7 Lett. l988,3, d) Black, T.H. ; tn3ay, W.J. ; lu.lly, P.S. J. Om. Cbem. 1988, - 53, 5922 and referenoes cited therein. 8. Black, T.H.; Maluleka, S.L. Tetrahedrcn Lett. 1989, 3, Obtained by the reaction of propanoic acid with two equivalents of m; see reference 7b. 10. Experimental details applicable to the synthesis of 2 and 3 are prwided in reference 7d. 11. Ratios were derived fmn integration of the vinyl protan abso&ances, or by canpariscn of peaks cornqxmhq ' tothe allylic ca.&mn atarrs (cf. Ccuperus, P.A.; Clarrgue, A.D.H.; van DcrucJen, J.P.C.M. Om. mu. Res. 1976, -8, 426 or de Haan, J.W.; van de V al L.J.M. && 1973, 3, 147). 12. Black, T.H.; Fields, J.D. svnth. CQRRm. 1988, u, Black, T.H.; Eisenbeis, S. svnth. ck-mmn., inpress. (Received in USA 19 May, 1989)
T. Howard Black a & Todd S. McDermott a a Department of Chemistry, Eastern Illinois
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