메뉴 건너뛰기




Volumn , Issue 18, 2008, Pages 3164-3170

Dialkylzinc-mediated atom transfer sequential radical addition cyclization

Author keywords

Enynes; Iodine atom transfer; Isomerization; Lactams; Radical reactions; Zinc

Indexed keywords


EID: 48749107507     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800242     Document Type: Article
Times cited : (32)

References (66)
  • 2
    • 0002036283 scopus 로고    scopus 로고
    • Eds: P. Renaud, M. Sibi, Wiley-VCH, Weinheim
    • b) J. Byers in Radicals in Organic Synthesis (Eds: P. Renaud, M. Sibi), Wiley-VCH, Weinheim, 2001, vol. 1, pp. 72-88.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 72-88
    • Byers, J.1
  • 5
    • 0025784933 scopus 로고
    • For selected examples involving alkynes, see: a
    • For selected examples involving alkynes, see: a) D. P. Curran, D. Kim, K. Ziegler, Tetrahedron 1991, 47, 6189;
    • (1991) Tetrahedron , vol.47 , pp. 6189
    • Curran, D.P.1    Kim, D.2    Ziegler, K.3
  • 7
    • 32344451178 scopus 로고    scopus 로고
    • For recent applications of I-ATRA and I-ATRC, see: a
    • For recent applications of I-ATRA and I-ATRC, see: a) P. Balczewski, A. Szadowiak, T. Bialas, Heteroat. Chem. 2006, 17, 22;
    • (2006) Heteroat. Chem , vol.17 , pp. 22
    • Balczewski, P.1    Szadowiak, A.2    Bialas, T.3
  • 9
    • 1842607534 scopus 로고    scopus 로고
    • For selected examples of triethylborane-mediated I-ATRC, see: a
    • For selected examples of triethylborane-mediated I-ATRC, see: a) O. Kitagawa, S. Miyaji, C. Sakuma, T. Taguchi, J. Org. Chem. 2004, 69, 2607;
    • (2004) J. Org. Chem , vol.69 , pp. 2607
    • Kitagawa, O.1    Miyaji, S.2    Sakuma, C.3    Taguchi, T.4
  • 15
    • 0033534067 scopus 로고    scopus 로고
    • For DIBAL-H mediated IATRC, see: g
    • For DIBAL-H mediated IATRC, see: g) A. Chakraborty, I. Marek, Chem. Commun. 1999, 2375.
    • (1999) Chem. Commun , pp. 2375
    • Chakraborty, A.1    Marek, I.2
  • 18
    • 33745026453 scopus 로고    scopus 로고
    • and references cited therein. For a review, see
    • For a review, see: S. Bazin, L. Feray, M. P. Bertrand, Chimia 2006, 60, 260 and references cited therein.
    • (2006) Chimia , vol.60 , pp. 260
    • Bazin, S.1    Feray, L.2    Bertrand, M.P.3
  • 30
    • 0003170224 scopus 로고    scopus 로고
    • II-induced radical reactions, see: a P. Knochel, Synlett 1995, 393;
    • II-induced radical reactions, see: a) P. Knochel, Synlett 1995, 393;
  • 33
    • 33646535639 scopus 로고    scopus 로고
    • For Pd-mediated reactions, see: a
    • For Pd-mediated reactions, see: a) W. Xu, A. Kong, X. Lu, J. Org. Chem. 2006, 71, 3854;
    • (2006) J. Org. Chem , vol.71 , pp. 3854
    • Xu, W.1    Kong, A.2    Lu, X.3
  • 37
    • 0001628288 scopus 로고
    • and previous notes cited therein
    • e) S. Ma, X. Lu, J. Org. Chem. 1991, 56, 5120 and previous notes cited therein.
    • (1991) J. Org. Chem , vol.56 , pp. 5120
    • Ma, S.1    Lu, X.2
  • 38
    • 33747806634 scopus 로고    scopus 로고
    • For Rh-mediated reactions, see: a
    • For Rh-mediated reactions, see: a) J. U. Rhee, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 10674;
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 10674
    • Rhee, J.U.1    Krische, M.J.2
  • 43
    • 0024520675 scopus 로고
    • For the initial addition of a tributyltin radical to a triple bond see: a
    • For the initial addition of a tributyltin radical to a triple bond see: a) E. Lee, S. B. Ko, K. W. Jung, Tetrahedron Lett. 1989, 30, 827;
    • (1989) Tetrahedron Lett , vol.30 , pp. 827
    • Lee, E.1    Ko, S.B.2    Jung, K.W.3
  • 44
    • 0028920134 scopus 로고    scopus 로고
    • For the reverse regioselectivity, see also: Z. Wang, X. Lu, Tetrahedron 1995, 51, 2639.
    • b) For the reverse regioselectivity, see also: Z. Wang, X. Lu, Tetrahedron 1995, 51, 2639.
  • 49
    • 53749086127 scopus 로고    scopus 로고
    • The assignments are based on the chemical shifts of the vinylic proton being more shielded in the Z isomer than in the E isomer: 6.59 ppm in (E)-2/5.59 ppm in (Z)-2; 6.42 ppm in (E)-3/5.73 ppm in (Z)-3; 6.27 ppm in (E)-4; 6.43 ppm in (E)-6.
    • The assignments are based on the chemical shifts of the vinylic proton being more shielded in the Z isomer than in the E isomer: 6.59 ppm in (E)-2/5.59 ppm in (Z)-2; 6.42 ppm in (E)-3/5.73 ppm in (Z)-3; 6.27 ppm in (E)-4; 6.43 ppm in (E)-6.
  • 54
    • 53749098743 scopus 로고    scopus 로고
    • According to a referee comment, the formation of G from A and similarly the formation of D from B might involve electron transfer from dialkylzinc rather than direct bimolecular homolytic substitution.
    • According to a referee comment, the formation of G from A and similarly the formation of D from B might involve electron transfer from dialkylzinc rather than direct bimolecular homolytic substitution.
  • 55
    • 0000679160 scopus 로고    scopus 로고
    • An alternative explanation would involve an iodine/zinc exchange between iodide 3 and diethylzinc. A reduction pathway involving iodine/magnesium exchange has been proposed for EtMgBr-promoted radical cyclization of iodoacetals, see: A. Inoue, H. Shinokubo, K. Oshima, Org. Lett. 2000, 2, 651
    • An alternative explanation would involve an iodine/zinc exchange between iodide 3 and diethylzinc. A reduction pathway involving iodine/magnesium exchange has been proposed for EtMgBr-promoted radical cyclization of iodoacetals, see: A. Inoue, H. Shinokubo, K. Oshima, Org. Lett. 2000, 2, 651.
  • 58
    • 53749096165 scopus 로고    scopus 로고
    • 2Zn and only 5 equiv. of tBuI.
    • 2Zn and only 5 equiv. of tBuI.
  • 62
    • 0001049972 scopus 로고
    • Knochel has demonstrated that RZnI derivatives tolerate the presence of acidic protons, in particular those of terminal non-activated alkynes, see
    • Knochel has demonstrated that RZnI derivatives tolerate the presence of acidic protons, in particular those of terminal non-activated alkynes, see: H. P. Knoess, M. T. Furlong, M. J. Rozema, P. Knochel, J. Org. Chem. 1991, 56, 5974.
    • (1991) J. Org. Chem , vol.56 , pp. 5974
    • Knoess, H.P.1    Furlong, M.T.2    Rozema, M.J.3    Knochel, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.