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Volumn 75, Issue 13, 2010, Pages 4652-4655

Stereocontrolled synthesis of trans-cyclopropyl sulfones from terminal epoxides

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPYL; DIASTEREO-SELECTIVITY; ENANTIOPURE; SODIUM SALT; STEREOCONTROLLED SYNTHESIS; TERMINAL EPOXIDE;

EID: 77954110998     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100844g     Document Type: Article
Times cited : (18)

References (67)
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    • Cyclopropane-containing drugs accounted for >$7 billion in sales in 2006. For a review of recent peptidomimetic approaches, see
    • Cyclopropane-containing drugs accounted for >$7 billion in sales in 2006. For a review of recent peptidomimetic approaches, see: Youla, S. T. Acc. Chem. Res. 2008, 41, 1252
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    • Examples of Wadsworth-Emmons cyclopropanation in synthesis are as follows
    • Examples of Wadsworth-Emmons cyclopropanation in synthesis are as follows: Delhaye, L.; Merschaert, A.; Delbeke, P.; Briône, W. Org. Process Res. Dev. 2007, 11, 689
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    • For the analogous, but less facile, use of phosphoranylidenes
    • For the analogous, but less facile, use of phosphoranylidenes, see: Denney, D. B.; Vill, J. J.; Boskin, M. J. J. Am. Chem. Soc. 1962, 84, 3944
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    • Wadsworth and Emmons have reported an isolated example of the use of the diethyl cyanomethylphosphonate for the conversion of styrene oxide to the corresponding cyanocyclopropane (51% yield); see ref 9
    • Wadsworth and Emmons have reported an isolated example of the use of the diethyl cyanomethylphosphonate for the conversion of styrene oxide to the corresponding cyanocyclopropane (51% yield); see ref 9.
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    • Katritzky et al. have reported three examples of an analogous cyclopropanation using 1-(benzotriazol-1-yl)diphenylphosphine oxide; see
    • Katritzky et al. have reported three examples of an analogous cyclopropanation using 1-(benzotriazol-1-yl)diphenylphosphine oxide; see: Katrizky, A. R.; Wu, H.; Xie, L.; Jiang, J. J. Heterocycl. Chem. 1995, 32, 595.
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    • An example of the protonated intermediate 4 has been detected by LC/MS; see ref 10d
    • An example of the protonated intermediate 4 has been detected by LC/MS; see ref 10d.
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    • Reaction between (S)-propylene oxide and 1a has been reported to give up to 95% yield with dr >98:2; see ref 10a
    • Reaction between (S)-propylene oxide and 1a has been reported to give up to 95% yield with dr >98:2; see ref 10a.
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    • Cyclopropyl sulfones can be subjected to alkylation/acylation; see
    • Cyclopropyl sulfones can be subjected to alkylation/acylation; see: Chang, Y. H.; Pinnick, H. W. J. Org. Chem. 1978, 43, 373
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    • They can be converted to methylene cyclopropanes
    • They can be converted to methylene cyclopropanes; see: Baldwin, J. E.; Adlington, R. M.; Bebbington, D. Tetrahedron 1994, 50, 12015
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    • They can form π-allyl palladium complexes which undergo reactions with electron deficient alkenes
    • They can form π-allyl palladium complexes which undergo reactions with electron deficient alkenes; see: Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871
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    • They can undergo desulfonylation to give simple cyclopropanes
    • They can undergo desulfonylation to give simple cyclopropanes; see: Kazuta, Y.; Matsuda, A.; Shuto, S. J. Org. Chem. 2002, 67, 1669
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    • They can act as synthons for 1,3-dipoles
    • They can act as synthons for 1,3-dipoles; see: Trost, B. M.; Cossy, J.; Burkes, J. J. Am. Chem. Soc. 1983, 105, 1052
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    • They can participate in Julia-type olefinations
    • They can participate in Julia-type olefinations; see: Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Synlett 2004, 1064
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    • Diethyl (phenylsulfonyl)methylphosphonate 6a is readily available via an Arbusov reaction between triethyl phosphite and chloromethyl phenyl sulfide and oxidation of the resultant product with Oxone; see the Supporting Information
    • Diethyl (phenylsulfonyl)methylphosphonate 6a is readily available via an Arbusov reaction between triethyl phosphite and chloromethyl phenyl sulfide and oxidation of the resultant product with Oxone; see the Supporting Information.
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    • 1H NMR spectroscopy (NOE, coupling constant analysis and comparison with data in ref 17b) and ultimately by X-ray crystallographic analysis of 9b, f; see the Supporting Information
    • 1H NMR spectroscopy (NOE, coupling constant analysis and comparison with data in ref 17b) and ultimately by X-ray crystallographic analysis of 9b, f; see the Supporting Information.
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    • Temperatures of up to 150 °C have been found to be beneficial in the reaction between 1b and propylene oxide; see ref 10b
    • Temperatures of up to 150 °C have been found to be beneficial in the reaction between 1b and propylene oxide; see ref 10b.
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    • Sulfone anion 6b has previously been used for the synthesis of vinyl sulfones. While in these cases transfer of diethyl phosphite also occurs in preference to the sulfone and competitive formation of vinyl phosphonates is not observed, such reactions are carried out at room temperature or below
    • Sulfone anion 6b has previously been used for the synthesis of vinyl sulfones. While in these cases transfer of diethyl phosphite also occurs in preference to the sulfone and competitive formation of vinyl phosphonates is not observed, such reactions are carried out at room temperature or below.
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    • Chiral methylene cyclopropanes have been used in tandem rhodium-catalyzed C-H activation/cycloisomerization reactions; see
    • Chiral methylene cyclopropanes have been used in tandem rhodium-catalyzed C-H activation/cycloisomerization reactions; see: Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.