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Volumn 45, Issue 35, 2006, Pages 5863-5866

Enantioselective cascade radical addition-cyclization-trapping reactions

Author keywords

Asymmetric synthesis; Enantioselectivity; Lactams; Lewis acids; Radical reactions

Indexed keywords

ACIDS; CATALYST SELECTIVITY; ESTERS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33748547632     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602042     Document Type: Article
Times cited : (54)

References (58)
  • 1
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    • For general information on enantioselective radical reactions, see: a) P. Renaud, M. Gerster, Angew. Chem. 1998, 110, 2704;
    • (1998) Angew. Chem. , vol.110 , pp. 2704
    • Renaud, P.1    Gerster, M.2
  • 6
  • 16
    • 33748536687 scopus 로고    scopus 로고
    • For selected examples of enantioselective hydrogen-atom transfer reactions, see: a) M. P. Sibi, K. Patil, Angew. Chem. 2004, 116, 1255;
    • (2004) Angew. Chem. , vol.116 , pp. 1255
    • Sibi, M.P.1    Patil, K.2
  • 34
    • 0041963076 scopus 로고    scopus 로고
    • For hydroxamic acid derivatives explored as achiral templates in the Diels-Alder reaction, see: a) O. Corminboeuf, P. Renaud, Org. Lett. 2002, 4, 1731;
    • (2002) Org. Lett. , vol.4 , pp. 1731
    • Corminboeuf, O.1    Renaud, P.2
  • 40
    • 33748225421 scopus 로고    scopus 로고
    • see also reference [1a]
    • Angew. Chem. Int. Ed. Engl 1996, 35, 190; see also reference [1a].
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 190
  • 45
    • 33748568755 scopus 로고    scopus 로고
    • note
    • 1H NMR study of 1a in the presence of a chiral Lewis acid is provided in the Supporting Information: a downfield shift in the chemical shifts of hydrogen atoms around the hydroxamate ester moiety was observed.
  • 46
    • 0000526974 scopus 로고    scopus 로고
    • For a report on a similar inversion in configuration, see: M. P. Sibi, J. Ji, J. Org. Chem. 1997, 62, 3800.
    • (1997) J. Org. Chem. , vol.62 , pp. 3800
    • Sibi, M.P.1    Ji, J.2
  • 47
    • 0029804421 scopus 로고    scopus 로고
    • In general, the combination of phenyl-substituted bis(oxazoline) (box) ligand and zinc Lewis acid gives high selectivity, whereas the aliphatic-substituted box ligands give high selectivity in combination with magnesium Lewis acids; see: a) M. P. Sibi, J. Ji, J. Am. Chem. Soc. 1996, 118, 9200;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9200
    • Sibi, M.P.1    Ji, J.2
  • 51
    • 33748528085 scopus 로고    scopus 로고
    • see the Supporting Information
    • The absolute configuration at the newly formed stereocenter of 8 could not be determined. The relative configuration of trans and cis diastereomers 8 Aa was determined by NOESY experiments (see the Supporting Information).
  • 52
    • 33751499942 scopus 로고
    • For discussions on atom-transfer cyclization, see: a) D. P. Curran, J. Tamine, J. Org. Chem. 1991, 56, 2746;
    • (1991) J. Org. Chem. , vol.56 , pp. 2746
    • Curran, D.P.1    Tamine, J.2
  • 56
    • 15444364845 scopus 로고    scopus 로고
    • The chiral substrate of (R)-9 (81 % ee) was prepared by our method using an iridium catalyst and the pyridinebis(oxazoline)-(pybox) ligand; see: a) H. Miyabe, K. Yoshida, M. Yamauchi, Y. Takemoto, J. Org. Chem. 2005, 70, 2148;
    • (2005) J. Org. Chem. , vol.70 , pp. 2148
    • Miyabe, H.1    Yoshida, K.2    Yamauchi, M.3    Takemoto, Y.4
  • 58
    • 33748544575 scopus 로고    scopus 로고
    • note
    • Details are provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.