메뉴 건너뛰기




Volumn 13, Issue 6, 2007, Pages 1692-1708

Bromoallenes as allyl dication equivalents in the presence or absence of palladium(0): Direct construction of bicyclic sulfamides containing five- to eight-membered rings by tandem cyclization of bromoallenes

Author keywords

Allenes; Cyclization; Heterocycles; Palladium; Tandem reactions

Indexed keywords

CARBON; CATALYSTS; CYCLIZATION; PALLADIUM; REACTION KINETICS;

EID: 34250666515     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601373     Document Type: Article
Times cited : (38)

References (88)
  • 18
    • 0033403666 scopus 로고    scopus 로고
    • L. Ducry, S. Reinelt, P. Seiler, F. Diederich, Helv. Chim. Acta 1999, 82, 2432-2447; see also reference [10a].
    • b) L. Ducry, S. Reinelt, P. Seiler, F. Diederich, Helv. Chim. Acta 1999, 82, 2432-2447; see also reference [10a].
  • 24
    • 0011133965 scopus 로고
    • a) M. Preiss, Chem. Ber. 1978, 111, 1915-1921;
    • (1978) Chem. Ber , vol.111 , pp. 1915-1921
    • Preiss, M.1
  • 26
    • 0033544412 scopus 로고    scopus 로고
    • C. Nuckolls, F. Hof, T. Martin, J. Rebek Jr., J. Am. Chem. Soc. 1999, 121, 10281-10285.
    • c) C. Nuckolls, F. Hof, T. Martin, J. Rebek Jr., J. Am. Chem. Soc. 1999, 121, 10281-10285.
  • 27
    • 9244261748 scopus 로고    scopus 로고
    • Recently, synthesis of cyclic sulfamides by the reaction of amino alcohols with Burgess-type reagent under mild conditions was reported, see: a
    • Recently, synthesis of cyclic sulfamides by the reaction of amino alcohols with Burgess-type reagent under mild conditions was reported, see: a) K. C. Nicolaou, D. A. Longbottom, S.A. Snyder. A.Z. Nalbanadian, X. Huang, Angew. Chem. 2002, 114, 4022-4026;
    • (2002) Angew. Chem , vol.114 , pp. 4022-4026
    • Nicolaou, K.C.1    Longbottom, D.A.2    Snyder, S.A.3    Nalbanadian, A.Z.4    Huang, X.5
  • 28
    • 0037131479 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3866-3870;
    • (2002) Chem. Int. Ed , vol.41 , pp. 3866-3870
    • Angew1
  • 29
    • 0042034174 scopus 로고    scopus 로고
    • For a related reaction of amino acid derivatives with chlorosulfonyl isocyanate, see
    • b) For a related reaction of amino acid derivatives with chlorosulfonyl isocyanate, see: Z. Regaïnia, M. Abdaoui, N.-E. Aouf, G. Dewynter, J.-L. Montero, Tetrahedron 2000, 56, 381-387.
    • (2000) Tetrahedron , vol.56 , pp. 381-387
    • Regaïnia, Z.1    Abdaoui, M.2    Aouf, N.-E.3    Dewynter, G.4    Montero, J.-L.5
  • 36
    • 0029983326 scopus 로고    scopus 로고
    • Reductive cross-coupling reaction of dibenzylidene sulfamides with zinc was also reported: S.V. Pansare, M. G. Malusare, Tetrahedron Lett. 1996, 37, 2859-2862.
    • Reductive cross-coupling reaction of dibenzylidene sulfamides with zinc was also reported: S.V. Pansare, M. G. Malusare, Tetrahedron Lett. 1996, 37, 2859-2862.
  • 37
    • 16244408580 scopus 로고    scopus 로고
    • Eds, N. Krause, A. S. K. Hashmi, Wiiey-VCH, Weinheim
    • S. Ma, in Modern Allene Chemistry, Vol. 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiiey-VCH, Weinheim, 2004, pp. 614-619.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 614-619
    • Ma, S.1
  • 41
    • 0038076018 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1749-1753;
    • (2003) Chem. Int. Ed , vol.42 , pp. 1749-1753
    • Angew1
  • 44
    • 22944443399 scopus 로고    scopus 로고
    • For a recent review, see:, Eds, N. Krause, A. S. K. Hashmi, Wiley-VCH, Weinheim
    • For a recent review, see: S. Ma, in Modern Allene Chemistry, Vol. 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 595-684.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 595-684
    • Ma, S.1
  • 45
    • 0000328530 scopus 로고
    • For organocopper-mediated substitutions, see: a
    • For organocopper-mediated substitutions, see: a) E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1984, 25, 3059-3062;
    • (1984) Tetrahedron Lett , vol.25 , pp. 3059-3062
    • Corey, E.J.1    Boaz, N.W.2
  • 51
    • 0012114207 scopus 로고
    • For palladium-catalyzed cross-coupling reactions, see: a
    • For palladium-catalyzed cross-coupling reactions, see: a) G. Märkl, P. Attenberger, J. Kellner, Tetrahedron Lett. 1988, 29, 3651-3654;
    • (1988) Tetrahedron Lett , vol.29 , pp. 3651-3654
    • Märkl, G.1    Attenberger, P.2    Kellner, J.3
  • 54
    • 0001652206 scopus 로고    scopus 로고
    • For the formation of nucleophilic allenyl metal reagents, see: a
    • For the formation of nucleophilic allenyl metal reagents, see: a) J. A. Marshall, N. D. Adams. J. Org. Chem. 1997, 62, 8976-8977;
    • (1997) J. Org. Chem , vol.62 , pp. 8976-8977
    • Marshall, J.A.1    Adams, N.D.2
  • 56
    • 34250639497 scopus 로고    scopus 로고
    • A portion of this study on the palladium-free cyclization yielding cyclosulfamides bearing a bicyclo[3.3.0] skeleton was already reported in a preliminary communication: H. Hamaguchi, S. Kosaka, H. Ohno, T. Tanaka, Angew. Chem. 2005, 117, 1537-1541;
    • A portion of this study on the palladium-free cyclization yielding cyclosulfamides bearing a bicyclo[3.3.0] skeleton was already reported in a preliminary communication: H. Hamaguchi, S. Kosaka, H. Ohno, T. Tanaka, Angew. Chem. 2005, 117, 1537-1541;
  • 57
    • 16244407181 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1513-1517.
    • (2005) Chem. Int. Ed , vol.44 , pp. 1513-1517
    • Angew1
  • 64
    • 34250667600 scopus 로고    scopus 로고
    • For synthesis of the propargyl alcohol (±)-7e, see the Supporting Information.
    • For synthesis of the propargyl alcohol (±)-7e, see the Supporting Information.
  • 65
    • 34250638716 scopus 로고    scopus 로고
    • 3OD. Therefore, it is apparent that the isomer 11a is thermodynamically more stable than the isomer 16a. At the present stage of our understanding, preferential formation of the relatively unstable isomer 16a by the reaction with TBAF/THF over the isomer 11a is unclear.
    • 3OD. Therefore, it is apparent that the isomer 11a is thermodynamically more stable than the isomer 16a. At the present stage of our understanding, preferential formation of the relatively unstable isomer 16a by the reaction with TBAF/THF over the isomer 11a is unclear.
  • 66
    • 34250656624 scopus 로고    scopus 로고
    • Structure of trans-12e and cis-12e′ were determined by comparison of / values of the ring protons, as shown below. Figure presented
    • Structure of trans-12e and cis-12e′ were determined by comparison of / values of the ring protons, as shown below. Figure presented
  • 67
    • 34250645011 scopus 로고    scopus 로고
    • The structure of 11i was determined by NOE analysis. Figure presented
    • The structure of 11i was determined by NOE analysis. Figure presented
  • 68
    • 34250619249 scopus 로고    scopus 로고
    • The phenyl group of 9i promotes the regioselective cyclization onto the central allenic carbon, presumably through a highly conjugated anionic transition state A and/or intermediate B. Figure presented
    • The phenyl group of 9i promotes the regioselective cyclization onto the central allenic carbon, presumably through a highly conjugated anionic transition state A and/or intermediate B. Figure presented
  • 69
    • 34250628085 scopus 로고    scopus 로고
    • Formation of the alkyne 18i can be rationalized by addition-elimination mechanism. One plausible pathway is shown below.
    • Formation of the alkyne 18i can be rationalized by addition-elimination mechanism. One plausible pathway is shown below.
  • 70
    • 34250639498 scopus 로고    scopus 로고
    • A similar result was obtained by the cyclization in the presence of palladium0, although the yield was lower, as shown below
    • A similar result was obtained by the cyclization in the presence of palladium(0), although the yield was lower, as shown below.
  • 71
    • 0028150852 scopus 로고    scopus 로고
    • Related five-membered ring formations by intramolecular amination of carbon-carbon triple bond have been already reported, see: a Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, Z. Yoshida, Bull. Chem. Soc. Jpn. 1994, 67, 2838-2849;
    • Related five-membered ring formations by intramolecular amination of carbon-carbon triple bond have been already reported, see: a) Y. Tamaru, M. Kimura, S. Tanaka, S. Kure, Z. Yoshida, Bull. Chem. Soc. Jpn. 1994, 67, 2838-2849;
  • 74
    • 34250617963 scopus 로고    scopus 로고
    • Isolation of 20′b was extremely difficult due to the hydrolysis during purification, yielding a ring-opening product 23 b. Accordingly, 23b was isolated in 70% yield after acidic workup and fully characterized.
    • Isolation of 20′b was extremely difficult due to the hydrolysis during purification, yielding a ring-opening product 23 b. Accordingly, 23b was isolated in 70% yield after acidic workup and fully characterized.
  • 75
    • 34250661137 scopus 로고    scopus 로고
    • 1NMR analysis of which showed formation of 20′b and 21b (2.5:1) quantitatively, without detecting 23b.
    • 1NMR analysis of which showed formation of 20′b and 21b (2.5:1) quantitatively, without detecting 23b.
  • 76
    • 34250687975 scopus 로고    scopus 로고
    • To reveal the intermediate of this tandem cyclization reaction, we investigated stepwise reaction of the bromoallene 24. Treatment of the bromoallene 24 with NaH in DMF gave piperidine 78 in 79% yield. Reaction of 78 under the same reaction conditions as the one-pot reaction afforded the exo-cyclized product 29 (93 %) as a single isomer.
    • To reveal the intermediate of this tandem cyclization reaction, we investigated stepwise reaction of the bromoallene 24. Treatment of the bromoallene 24 with NaH in DMF gave piperidine 78 in 79% yield. Reaction of 78 under the same reaction conditions as the one-pot reaction afforded the exo-cyclized product 29 (93 %) as a single isomer.
  • 77
    • 34250613139 scopus 로고    scopus 로고
    • Structure of (±)-32 was confirmed by NOE analysis as shown below. Figure presented
    • Structure of (±)-32 was confirmed by NOE analysis as shown below. Figure presented
  • 78
    • 34250628502 scopus 로고    scopus 로고
    • The reaction of 27 with NaH in MeOH afforded an inseparable mixture of (E)- and (Z)-enynes, produced by elimination of HBr under the basic reaction conditions.
    • The reaction of 27 with NaH in MeOH afforded an inseparable mixture of (E)- and (Z)-enynes, produced by elimination of HBr under the basic reaction conditions.
  • 79
    • 34250636369 scopus 로고    scopus 로고
    • 1H NMR spectroscopy.
    • 1H NMR spectroscopy.
  • 80
    • 34250649770 scopus 로고    scopus 로고
    • 4] was ineffective: only 15% of the cyclosulfamide 49 and a trace amount of 32, produced by the uncatalyzed reaction (Table 5), were obtained.
    • 4] was ineffective: only 15% of the cyclosulfamide 49 and a trace amount of 32, produced by the uncatalyzed reaction (Table 5), were obtained.
  • 81
    • 34250681437 scopus 로고    scopus 로고
    • Without treatment with HC1, the ratio of regioisomers (products of the type 53 and 54) is variable.
    • Without treatment with HC1, the ratio of regioisomers (products of the type 53 and 54) is variable.
  • 82
    • 34250646677 scopus 로고    scopus 로고
    • The palladium-catalyzed cyclization of bromoallene 79 having a six-atom tether between the sulfamide and allenyl group gave a trace of the desired tricyclic sulfamide 80 containing a nine-membered ring (<5% yield). Figure presented
    • The palladium-catalyzed cyclization of bromoallene 79 having a six-atom tether between the sulfamide and allenyl group gave a trace of the desired tricyclic sulfamide 80 containing a nine-membered ring (<5% yield). Figure presented
  • 83
    • 34250682668 scopus 로고    scopus 로고
    • Treatment of bromoallene 65 with NaOMe in DMF gave azetidine 81 as a major product and a small amount of dihydropyrrole 67 having a methoxymethyl group. We have already reported the formation of azetidines by NaH-mediated intramolecular amination of bromoallenes: see. reference [13b, Figure presented
    • Treatment of bromoallene 65 with NaOMe in DMF gave azetidine 81 as a major product and a small amount of dihydropyrrole 67 having a methoxymethyl group. We have already reported the formation of azetidines by NaH-mediated intramolecular amination of bromoallenes: see. reference [13b]. Figure presented
  • 88
    • 0032481404 scopus 로고    scopus 로고
    • In the reaction of propargylic carbonates, it is proposed that the first nucleophilic addition onto the η3-propargylpalladium produces a metallacyclobutene, protonation of which generates the η3- allylpalla- dium complex: C. P. Casey, J. R. Nash, C. S. Yi, A. D. Selmeczy, S. Chung, D. R. Powell, R. K. Hayashi, J. Am. Chem. Soc. 1998, 120, 722-733
    • 3- allylpalla- dium complex: C. P. Casey, J. R. Nash, C. S. Yi, A. D. Selmeczy, S. Chung, D. R. Powell, R. K. Hayashi, J. Am. Chem. Soc. 1998, 120, 722-733.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.