메뉴 건너뛰기




Volumn 76, Issue 12, 2011, Pages 4952-4963

SmI2-mediated radical cross-couplings of α-hydroxylated aza-hemiacetals and N, S -acetals with α,β-unsaturated compounds: Asymmetric synthesis of (+)-hyacinthacine A2, (-)-uniflorine A, and (+)-7- epi -casuarine

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CONTROLLED EXPERIMENT; COUPLING REACTION; CROSS-COUPLINGS; MEDIATED REACTIONS; N ,S-ACETALS; PYRROLIDINES; RADICAL COUPLING REACTIONS; RADICAL MECHANISM; SWITCHABLE;

EID: 79958847766     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200600n     Document Type: Article
Times cited : (55)

References (112)
  • 6
    • 0034625424 scopus 로고    scopus 로고
    • For recent reviews on N -acyliminium based C-C bond formation methods, see
    • For recent reviews on N -acyliminium based C-C bond formation methods, see: Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 8
    • 33846065375 scopus 로고    scopus 로고
    • part 1, at
    • Marson, C. M. Arkivoc 2001, part 1, 1-16, at www.arkat-usa.org.
    • (2001) Arkivoc , pp. 1-16
    • Marson, C.M.1
  • 10
    • 2942574530 scopus 로고    scopus 로고
    • Royer, J. Chem. Rev. 2004, 104, 2311-2352
    • (2004) Chem. Rev. , vol.104 , pp. 2311-2352
    • Royer, J.1
  • 12
    • 63549102143 scopus 로고    scopus 로고
    • For recent reviews on Mannich reaction, see:;; Angew. Chem., Int. Ed. 1998, 1044-1070
    • Yazici, A.; Pyne, S. G. Synthesis 2009, 513-541 For recent reviews on Mannich reaction, see: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070
    • (2009) Synthesis , vol.37 , pp. 513-541
    • Yazici, A.1    Pyne, S.G.2    Arend, M.3    Westermann, B.4    Risch, N.5
  • 14
    • 0000679903 scopus 로고    scopus 로고
    • For reviews involving the generation and application of α-lithioamines, see
    • For reviews involving the generation and application of α-lithioamines, see: Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560
    • (1996) Acc. Chem. Res. , vol.29 , pp. 552-560
    • Beak, P.1    Basu, A.2    Gallagher, D.J.3    Park, Y.S.4    Thayumanavan, S.5
  • 19
    • 0029789351 scopus 로고    scopus 로고
    • For reviews on α-aminoalkyl radicals, see
    • For reviews on α-aminoalkyl radicals, see: Renaud, P.; Giraud, L. Synthesis 1996, 913-926
    • (1996) Synthesis , pp. 913-926
    • Renaud, P.1    Giraud, L.2
  • 23
    • 65249146649 scopus 로고    scopus 로고
    • For a recent review on metal-mediated α-amino C-C bond formation, see:, For selected examples, see:;; J. Am. Chem. Soc. 2006, 128, 14220-14221
    • For a recent review on metal-mediated α-amino C-C bond formation, see: Li, C.-J. Acc. Chem. Res. 2009, 42, 335-344 For selected examples, see: Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220-14221
    • (2009) Acc. Chem. Res. , vol.42 , pp. 335-344
    • Li, C.-J.1    Pastine, S.J.2    Gribkov, D.V.3    Sames, D.4
  • 29
  • 32
    • 41549130872 scopus 로고    scopus 로고
    • For selected recent application, see:;; J. Am. Chem. Soc. 2008, 130, 1136-1137
    • Gopalaiah, K.; Kagan, H. B. New J. Chem. 2008, 32, 607-637 For selected recent application, see: Duffy, L. A.; Matsubara, H.; Procter, D. J. J. Am. Chem. Soc. 2008, 130, 1136-1137
    • (2008) New J. Chem. , vol.32 , pp. 607-637
    • Gopalaiah, K.1    Kagan, H.B.2    Duffy, L.A.3    Matsubara, H.4    Procter, D.J.5
  • 54
    • 29744450315 scopus 로고    scopus 로고
    • 2/proton source mediated radical coupling reactions of α,β-unsaturated compounds with ketones, see:;;; J. Chem. Soc., Chem. Commun 1986, 624-625
    • 2/proton source mediated radical coupling reactions of α,β-unsaturated compounds with ketones, see: Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun 1986, 624-625
    • (2005) Synlett , pp. 3019-3032
    • Jung, D.Y.1    Kim, Y.H.2    Fukuzawa, S.3    Nakanishi, A.4    Fujinami, T.5    Sakai, S.6
  • 62
    • 0002500003 scopus 로고    scopus 로고
    • 2-mediated C-C bond formation based on the homocleavage of C-S bond, see
    • 2-mediated C-C bond formation based on the homocleavage of C-S bond, see: Urban, D.; Skrydstrup, T.; Beau, J. M. Chem. Commun. 1998, 955-956
    • (1998) Chem. Commun. , pp. 955-956
    • Urban, D.1    Skrydstrup, T.2    Beau, J.M.3
  • 65
    • 0037161860 scopus 로고    scopus 로고
    • For selected methods on the preparation of aza-hemiacetals and N, O -acetals, see
    • For selected methods on the preparation of aza-hemiacetals and N, O -acetals, see: Suh, Y. G.; Shin, D. Y.; Jung, J. K.; Kim, S. H. Chem. Commun. 2002, 1064-1065
    • (2002) Chem. Commun. , pp. 1064-1065
    • Suh, Y.G.1    Shin, D.Y.2    Jung, J.K.3    Kim, S.H.4
  • 70
    • 84990135406 scopus 로고
    • For reviews on the stereoselective radical reactions, see
    • For reviews on the stereoselective radical reactions, see: Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969-980
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 969-980
    • Giese, B.1
  • 90
    • 51649092172 scopus 로고    scopus 로고
    • For the structural reversion of uniflorine A, see
    • For the structural reversion of uniflorine A, see: Ritthiwigrom, T.; Pyne, S. G. Org. Lett. 2008, 10, 2769-2771
    • (2008) Org. Lett. , vol.10 , pp. 2769-2771
    • Ritthiwigrom, T.1    Pyne, S.G.2
  • 92
    • 75749099813 scopus 로고    scopus 로고
    • For the asymmetric synthesis of (-)-uniflorine A, see
    • For the asymmetric synthesis of (-)-uniflorine A, see: Ritthiwigrom, T.; Willis, A. C.; Pyne, S. G. J. Org. Chem. 2010, 75, 815-824
    • (2010) J. Org. Chem. , vol.75 , pp. 815-824
    • Ritthiwigrom, T.1    Willis, A.C.2    Pyne, S.G.3
  • 95
    • 0033592505 scopus 로고    scopus 로고
    • For asymmetric syntheses of casuarine, see
    • For asymmetric syntheses of casuarine, see: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311-1314
    • (1999) Org. Lett. , vol.1 , pp. 1311-1314
    • Denmark, S.E.1    Hurd, A.R.2
  • 99
    • 79958862136 scopus 로고    scopus 로고
    • Reference 27a
    • Reference 27a.
  • 105
    • 0000451948 scopus 로고    scopus 로고
    • For diastereoselective dihydroxylation of α,β-unsaturated amides, see:; Tetrahedron Lett. 1993, 34, 2079-2082
    • Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421-433 For diastereoselective dihydroxylation of α,β-unsaturated amides, see: Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2079-2082
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 421-433
    • Dupau, P.1    Epple, R.2    Thomas, A.A.3    Fokin, V.V.4    Sharpless, K.B.5    Bennani, Y.L.6    Sharpless, K.B.7
  • 109
    • 33751391316 scopus 로고
    • For the reductive dehydroxylation of aza-hemiacetals, see
    • For the reductive dehydroxylation of aza-hemiacetals, see: Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656-1662
    • (1992) J. Org. Chem. , vol.57 , pp. 1656-1662
    • Burgess, L.E.1    Meyers, A.I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.