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Volumn 11, Issue 6, 2005, Pages 1949-1957

Stereoselective allyl amine synthesis through enantioselective addition of diethylzinc and [1,3]-chirality transfer: Synthesis of lentiginosine and polyoxamic acid derivative

Author keywords

Asymmetric synthesis; Natural products; Rearrangement; Synthesis design; Total synthesis

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; DERIVATIVES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 15044347558     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400830     Document Type: Article
Times cited : (40)

References (59)
  • 6
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    • For a review of matched-mismatched problems, see: S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1; Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1
  • 44
    • 0029069807 scopus 로고
    • Aldehyde 9 was prepared in 90% yield by o-iodoxybenzoic acid (IBX) oxidation of the allyl alcohol 7. For the IBX oxidation, see: a) E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3485
    • Corey, E.J.1    Palani, A.2
  • 47
    • 15044338525 scopus 로고    scopus 로고
    • note
    • 1H NMR), which is consistent with the [1,3]-chirality transfer of the allyl cyanate-to-isocyanate rearrangement.
  • 49
    • 0001374523 scopus 로고
    • Although allyl cyanates such as A (Figure 7) have been considered to be possible intermediates in the reaction, there is also some experimental evidence of their involvement. See: a) K. Banert, Angew. Chem. 1992, 104, 865; Angew. Chem. Int. Ed. Engl. 1992, 31, 866;
    • (1992) Angew. Chem. , vol.104 , pp. 865
    • Banert, K.1
  • 50
    • 33748842050 scopus 로고
    • Although allyl cyanates such as A (Figure 7) have been considered to be possible intermediates in the reaction, there is also some experimental evidence of their involvement. See: a) K. Banert, Angew. Chem. 1992, 104, 865; Angew. Chem. Int. Ed. Engl. 1992, 31, 866;
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 866
  • 53
    • 33746236970 scopus 로고
    • a) P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 107, 2179; Angew. Chem. Int. Ed. Engl. 1995, 34, 2039;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2039
  • 57
    • 15044354367 scopus 로고    scopus 로고
    • note
    • For the inherent ring strain imposed by the trans-acetonide group, only the substitution product i was isolated by deprotection of the o-nosyl amide in 25. diagram presented


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.