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DOI: 10.1055/s-0028-1083315
Diastereoselective Synthesis of α-Stabilized Phosphorus Ylides via a Four-Component Reaction
Publication History
Publication Date:
09 January 2009 (online)
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Abstract
Functionalized and α-stabilized derivatives of dialkyl 2-{1-[(alkylamino)carbonyl]-2-oxopropyl}-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate were obtained in excellent yields from the reaction between primary amines, diketene, and dialkyl acetylenedicarboxylate in the presence of triphenylphosphine. Not only the reaction is diastereoselective but also the formed diasteromer has two rotamers that are in equilibrium with each other. ¹H, ¹³C, and ³¹P NMR showed only one of the two rotamers and thus conversion of Z-isomer into another is negligible at room temperature.
Key words
α-stabilized phosphorus ylide - triphenylphosphine - diketene - dialkyl acetylenedicarboxylate - multicomponent reaction - diastereoselective reaction
- 1
Wittig G. Science 1980, 210: 600 -
2a
Wittig G.Pohmer L. Chem. Ber. 1956, 89: 1334 -
2b
Wittig G.Geissler G. Liebigs Ann. Chem. 1953, 44: 580 -
2c
Staudinger H.Meyer J. Helv. Chim. Acta 1919, 2: 635 -
2d
Kolodiazhnyi OI. Phosphorus Ylides Wiley-VCH; Weinheim: 1999. - 3
Wittig G. Pure Appl. Chem. 1964, 9: 635 -
4a
Bestmann HJ.Graf G.Hartung H.Kolewa S.Vilsmaier E. Chem. Ber. 1970, 103: 2794 -
4b
Bestmann HJ.Hartung H. Chem. Ber. 1966, 99: 1198 -
4c
Lang RW.Hansen HJ. Helv. Chim. Acta 1980, 63: 438 -
4d
Marshall JA.Wolf MA.Wallace EM. J. Org. Chem. 1997, 62: 367 -
4e
Silveira CC.Boeck P.Braga AL. Tetrahedron Lett. 2000, 41: 1867 -
4f
Tomoskozi I.Bestmann HJ. Tetrahedron Lett. 1964, 1293 -
4g
Bestmann HJ.Tomoskozi I. Tetrahedron 1968, 26: 3299 -
5a
Runge W.Kresze G. Liebigs Ann. Chem. 1975, 1361 -
5b
Musierowicz S.Wroblewski AE. Tetrahedron 1980, 36: 1375 -
5c
Tanaka K.Fuji K. Tetrahedron Lett. 1996, 37: 3735 -
5d
Yamazaki J.Watanabe T.Tanaka K. Tetrahedron: Asymmetry 2001, 12: 669 -
6a
Shen Y. Acc. Chem. Res. 1998, 31: 584 -
6b
Puke C.Erker G.Aust NC.Würthwein EU.Fröhlich R. J. Am. Chem. Soc. 1998, 120: 4863 -
6c
Kolodiazhnyi OI. Russ. Chem. Rev. 1997, 66: 225 -
6d
Cherkasov RA.Pudovik MA. Russ. Chem. Rev. 1994, 63: 1019 -
6e
Pietrusiewiz KM.Zablocka M. Chem. Rev. 1994, 94: 1375 -
7a
Cobridge DEC. Phosphorus: An Outline of Chemistry, Biochemistry and Uses 5th ed.: Elsevier; Amsterdam: 1995. -
7b
Hudson HR. Primary, Secondary and Tertiary Phosphines, Polyphosphines and Heterocyclic Organophosphorus(III) Compounds, In The Chemistry of Organophosphorus Compounds Vol. 1:Hartley FR. Wiley; New York: 1990. p.386-472 -
7c
Engel R. Synthesis of Carbon-Phosphorus Bonds CRC; Boca Raton, FL: 1988. -
7d
Cadogan JIG. Organophosphorus Reagents in Organic Synthesis Academic; New York: 1979. -
7e
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863 - 8
Cristau HJ. Chem. Rev. 1994, 94: 1299 - 9
Kolodiazhnyl OI. Tetrahedron 1996, 52: 1855 - 10
Alizadeh A.Zohreh N.Rostamnia S. Tetrahedron 2007, 63: 8083 - 11
Alizadeh A.Zohreh N. Synthesis 2008, 429 - 12
Alizadeh A.Zohreh N. Helv. Chim. Acta 2008, 91: 844 - 13
Alizadeh A.Zohreh N.Zhu LG. Synthesis 2008, 2076 - 14
Zohreh N. Synlett 2008, 1913 -
15a
Yavari I.Alizadeh A.Anary-Abbasinejad M. Phosphorus Sulfur Silicon 2003, 178: 269 -
15b
Yavari I.Zabarjad-Shiraz N.Bijanzadeh HR. Phosphorus Sulfur Silicon 2004, 179: 1381 -
15c
Yavari I.Ramazani A.Yahya-Zadeh A. Synth. Commun. 1996, 26: 4495
References
CCDC 695672 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336 033; E-mail: mailto:deposit@ccdc.cam.ac.uk].