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Volumn 9, Issue 21, 2007, Pages 4363-4366

δ-Sultone formation through Rh-catalyzed C-H insertion

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; HETEROCYCLIC COMPOUND; NAPHTHALENESULFONIC ACID DERIVATIVE; NAPHTHOSULTONE; RHODIUM; UNCLASSIFIED DRUG;

EID: 35548934727     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701950d     Document Type: Article
Times cited : (76)

References (69)
  • 30
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    • Use of iodonium ylides as carbene precursors was originally advanced by Varvoglis and Moriarty, see: a
    • Use of iodonium ylides as carbene precursors was originally advanced by Varvoglis and Moriarty, see: (a) Hatjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. J. Chem. Soc., Perkin Trans. 1 1988, 2839-2846.
    • (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 2839-2846
    • Hatjiarapoglou, L.1    Varvoglis, A.2    Alcock, N.W.3    Pike, G.A.4
  • 37
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    • Thermal reactions of diazosulfonates to generate alkene products have been reported, see
    • Thermal reactions of diazosulfonates to generate alkene products have been reported, see: Berkessel, A.; Voges, M. Chem. Ber. 1989, 122, 1147-1151.
    • (1989) Chem. Ber , vol.122 , pp. 1147-1151
    • Berkessel, A.1    Voges, M.2
  • 38
    • 0016725064 scopus 로고
    • Sulfonyl chloride 2 was prepared following a modification of a procedure outlined by:, See the Supporting Information for details
    • Sulfonyl chloride 2 was prepared following a modification of a procedure outlined by: Oliver, J. E.; DeMilo, A. B. Synthesis 1975, 321-322. See the Supporting Information for details.
    • (1975) Synthesis , pp. 321-322
    • Oliver, J.E.1    DeMilo, A.B.2
  • 39
    • 84858345635 scopus 로고    scopus 로고
    • 3N were considerably less effective.
    • 3N were considerably less effective.
  • 40
    • 35548948134 scopus 로고    scopus 로고
    • Use of p-acetamidobenzenesulfonyl azide gave poor yield of the diazo compound and, instead, a significant amount of the alcohol, ROH, was generated
    • Use of p-acetamidobenzenesulfonyl azide gave poor yield of the diazo compound and, instead, a significant amount of the alcohol, ROH, was generated.
  • 41
    • 84858360757 scopus 로고    scopus 로고
    • Purified diazosulfonate derivatives are generally stable for weeks if stored at -20 °C In two cases (entries 2 and 4), decomposition was observed when these materials were left to stand overnight at 23 °C
    • Purified diazosulfonate derivatives are generally stable for weeks if stored at -20 °C In two cases (entries 2 and 4), decomposition was observed when these materials were left to stand overnight at 23 °C
  • 42
    • 84858356143 scopus 로고    scopus 로고
    • The addition of powdered 3 Åmolecular sieves was found to improve sultone yields in a few instances, see the Supporting Information for details.
    • The addition of powdered 3 Åmolecular sieves was found to improve sultone yields in a few instances, see the Supporting Information for details.
  • 43
    • 35548986330 scopus 로고    scopus 로고
    • Other Rh catalysts examined included Rh2(oct)4, Rh2(OPiV)4, Rh2(O2CCPh 3)4, Rh2(O2CCF3) 4, Rh2(NHCOCF3)4, and Rh 2(cap)4
    • 4.
  • 44
    • 35548986772 scopus 로고    scopus 로고
    • In entry 4, the five-membered-ring product formed through benzylic C-H insertion was also obtained (42% yield).
    • In entry 4, the five-membered-ring product formed through benzylic C-H insertion was also obtained (42% yield).
  • 45
    • 0042803335 scopus 로고
    • For select examples of transannular C-H insertions with diazoketones, see: a
    • For select examples of transannular C-H insertions with diazoketones, see: (a) Ghatak, U. R.; Chakrabarty, S. J. Am. Chem. Soc. 1972, 94, 4756-4758.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 4756-4758
    • Ghatak, U.R.1    Chakrabarty, S.2
  • 50
    • 0343163312 scopus 로고    scopus 로고
    • A typical y-sultone C-S-O bond angle is ≤98°, see: (a) Billodeaux, D. R.; Owens, C. V.; Sayes, C. M.; Soper, S. A.; Fronczek, F. R. Acta Cryst. 1999, C55, 2126-2129.
    • A typical y-sultone C-S-O bond angle is ≤98°, see: (a) Billodeaux, D. R.; Owens, C. V.; Sayes, C. M.; Soper, S. A.; Fronczek, F. R. Acta Cryst. 1999, C55, 2126-2129.
  • 52
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    • For select X-ray data of acyclic sulfonates and δ-sultones, see: (a) Ferguson, G.; Schwan, A. L.; Kalin, M. L.; Snelgrove, J. L. Acta Crystallogr. 1997, C53, IUC9700009.
    • For select X-ray data of acyclic sulfonates and δ-sultones, see: (a) Ferguson, G.; Schwan, A. L.; Kalin, M. L.; Snelgrove, J. L. Acta Crystallogr. 1997, C53, IUC9700009.
  • 54
    • 35548942816 scopus 로고    scopus 로고
    • We have used a similar argument to explain the strong bias for oxathiazinane dioxide formation in amination reactions of sulfamate esters, see ref 7a
    • We have used a similar argument to explain the strong bias for oxathiazinane dioxide formation in amination reactions of sulfamate esters, see ref 7a.
  • 57
    • 84987262316 scopus 로고    scopus 로고
    • Müller has demonstrated Rh-catalyzed C-H insertions of isolated iodonium ylides: Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958.
    • Müller has demonstrated Rh-catalyzed C-H insertions of isolated iodonium ylides: Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958.
  • 58
    • 9644254037 scopus 로고    scopus 로고
    • Rh2(esp)2, Rh 2(ααα′α′-tetramethyl-1, 3-benzenedipropionate)2, see: Espino, C G, Fiori, K. W, Kim, M, Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379. Interestingly, syringe-pump addition of Rh2(oct)4 over a 1 h period to a suspension of 4, PhI=O, Cs2CO3, and 3 ÅMS, gave results comparable to entry 7. The unique effectiveness of Rh2(OAc)4 as a catalyst for this process is absent a clear explanation at this time
    • 4 as a catalyst for this process is absent a clear explanation at this time.
  • 60
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    • For reviews on sultone synthesis and reactivity, see: a
    • For reviews on sultone synthesis and reactivity, see: (a) Roberts, D. W.; Williams, D. L. Tetrahedron 1987, 43, 1027-1062.
    • (1987) Tetrahedron , vol.43 , pp. 1027-1062
    • Roberts, D.W.1    Williams, D.L.2
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    • 3 upon heating with or without acid gave no reaction.
    • 3 upon heating with or without acid gave no reaction.
  • 63
    • 35548959702 scopus 로고    scopus 로고
    • Use of Zn dust alone resulted in conversion to the corresponding sulfinic acid, which proved resistant toward desulfinylation
    • Use of Zn dust alone resulted in conversion to the corresponding sulfinic acid, which proved resistant toward desulfinylation.
  • 64
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    • For related transformations, see: a
    • For related transformations, see: (a) Little, R. D.; Myong, S. O. Tetrahedron Lett. 1980, 21, 3339-3342
    • (1980) Tetrahedron Lett , vol.21 , pp. 3339-3342
    • Little, R.D.1    Myong, S.O.2
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    • (b) Hwu, J. R. J. Org. Chem. 1983, 48, 4432-4433.
    • (1983) J. Org. Chem , vol.48 , pp. 4432-4433
    • Hwu, J.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.