메뉴 건너뛰기




Volumn 19, Issue 2, 2013, Pages 678-684

Direct nucleophilic addition to N-alkoxyamides

Author keywords

allylation; amides; cyanation; nucleophilic addition; synthetic methods

Indexed keywords

CARBONYL GROUPS; CHELATED COMPLEX; CYANATION; DIISOBUTYLALUMINUM HYDRIDE; FUNCTIONALIZATIONS; HIGH STABILITY; INTRAMOLECULAR REACTIONS; NUCLEOPHILIC ADDITIONS; ONE POT; ORGANIC REACTION; ORGANOLITHIUM REAGENT; SYNTHESIS OF AMIDE; SYNTHETIC METHODS; VINYLATION;

EID: 84871960406     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202639     Document Type: Article
Times cited : (48)

References (107)
  • 6
    • 84864880988 scopus 로고    scopus 로고
    • For a review on the functionalization of carbonyl groups in ketones, esters, and amides, see:, D. Seebach, Angew. Chem. 2011, 123, 99-105
    • (2011) Angew. Chem. , vol.123 , pp. 99-105
    • Seebach, D.1
  • 24
    • 84855319390 scopus 로고    scopus 로고
    • T. Murai, Y. Mutoh, Chem. Lett. 2012, 41, 2-8. For selected examples of nucleophilic additions to acyclic thioamides, see
    • (2012) Chem. Lett. , vol.41 , pp. 2-8
    • Murai, T.1    Mutoh, Y.2
  • 35
    • 77951147307 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 3037-3040
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 3037-3040
  • 39
    • 84860757618 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 4572-4576
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4572-4576
  • 41
    • 84864883180 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 8314-8317. For chemoselective reduction of secondary amides to ketones and ketimines using triflic anhydride, see
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8314-8317
  • 44
    • 84861818014 scopus 로고    scopus 로고
    • Lu reported the synthesis of α-tertiary α-silylamines from aryl sulfonylimidates by using a related sequential nucleophilic addition, see:, X.-J. Han, M. Yao, C.-D. Lu, Org. Lett. 2012, 14, 2906-2909.
    • (2012) Org. Lett. , vol.14 , pp. 2906-2909
    • Han, X.-J.1    Yao, M.2    Lu, C.-D.3
  • 45
    • 84863070613 scopus 로고    scopus 로고
    • We reported the direct chemoselective allylation of tertiary and secondary amides with Schwartz reagent, see:, Y. Oda, T. Sato, N. Chida, Org. Lett. 2012, 14, 950-953; for selected examples of direct nucleophilic additions, see
    • (2012) Org. Lett. , vol.14 , pp. 950-953
    • Oda, Y.1    Sato, T.2    Chida, N.3
  • 47
    • 84871989072 scopus 로고
    • Diss. ETH Nr. 7935, ETH Zürich (CH)
    • M. Schiess, Diss. ETH Nr. 7935, ETH Zürich (CH), 1986
    • (1986)
    • Schiess, M.1
  • 52
    • 77956046302 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 6369-6372; for an example of direct conversion of N-alkoxyamides, see
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6369-6372
  • 54
    • 79551658706 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 1350-1353; Kibayashi reported pioneering work involving Grignard addition and subsequent hydride reduction to six-membered N-alkoxylactams, see
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1350-1353
  • 56
    • 27844466269 scopus 로고
    • S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818; for selected recent reviews on Weinreb amides, see
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 84
  • 106
    • 33845373996 scopus 로고
    • For a selected review on vinylsilane cyclization, see:, T. A. Blumenkopf, L. E. Overman, Chem. Rev. 1986, 86, 857-873.
    • (1986) Chem. Rev. , vol.86 , pp. 857-873
    • Blumenkopf, T.A.1    Overman, L.E.2
  • 107
    • 0000902959 scopus 로고
    • The reaction might proceed through a [3,3]-sigmatropic rearrangement and subsequent intramolecular allylation, see:, G. W. Daub, D. A. Heerding, L. E. Overman, Tetrahedron 1988, 44, 3919-3930.
    • (1988) Tetrahedron , vol.44 , pp. 3919-3930
    • Daub, G.W.1    Heerding, D.A.2    Overman, L.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.