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Volumn 62, Issue 44, 2006, Pages 10361-10378

Stereodivergent synthesis of 1,4-bifunctional compounds by regio- and diastereoselective Pd-catalyzed allylic substitution reaction

Author keywords

1,3 Asymmetric transfer; 1,4 Bifunctional compound; Catalytic reaction; Stereoselective reaction

Indexed keywords

ALCOHOL; CARBON; KETONE; LEAD; NITROGEN; SULFUR;

EID: 33748702060     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.057     Document Type: Article
Times cited : (10)

References (43)
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    • For application of olefins flanking two stereogenic centers to a sythesis of natural products, see:
  • 8
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    • Two methods have been developed so far; Pd-catalyzed allylic substitution reactions of cyclic carbonates and 1,3-diene monoepoxides, see:
  • 13
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    • For selected recent reviews for Pd-catalyzed allylic substitutions, see:
  • 24
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    • Clayden and co-workers reported the Pd-catalyzed rearrangement of allylic esters controlled by a dibenzylamino group. However, the regioselectivity depends on the acyl groups and is not sufficiently high, see:
    • Clayden and co-workers reported the Pd-catalyzed rearrangement of allylic esters controlled by a dibenzylamino group. However, the regioselectivity depends on the acyl groups and is not sufficiently high, see:. Clayden J., McCarthy C., and Cumming J.G. Tetrahedron: Asymmetry 9 (1998) 1427-1440
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1427-1440
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    • Related reaction using iodohexene, see:
    • Related reaction using iodohexene, see:. Chen M.-J., Narkunan K., and Liu R.-S. J. Org. Chem. 64 (1999) 8311-8318
    • (1999) J. Org. Chem. , vol.64 , pp. 8311-8318
    • Chen, M.-J.1    Narkunan, K.2    Liu, R.-S.3
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    • Precursors of π-allylpalladium complexes, see:
    • Precursors of π-allylpalladium complexes, see:. Tsuji J. Tetrahedron 42 (1986) 4361-4401
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    • note
    • All reactions were carried out using Pd catalyst (10 mol %), ligand (30 mol %), dibenzylamine (2 equiv) in refluxing THF.
  • 31
    • 2142858450 scopus 로고
    • 2-C and conversion to the corresponding MTPA esters. The R-configuration does not contradict the double inversion mechanism. Stereochemistry of other products was assumed by analogy of these results. For Modified Mosher method, see:
    • 2-C and conversion to the corresponding MTPA esters. The R-configuration does not contradict the double inversion mechanism. Stereochemistry of other products was assumed by analogy of these results. For Modified Mosher method, see:. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092-4096
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
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    • For the Carreira's asymmetric alkynylation, see:
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    • Nucleophilic addition to the acetonide-protected glyceraldehyde regularly affords poor selectivity; see:
    • Nucleophilic addition to the acetonide-protected glyceraldehyde regularly affords poor selectivity; see:. Mead K., and Macdonald T.L. J. Org. Chem. 50 (1985) 422-424
    • (1985) J. Org. Chem. , vol.50 , pp. 422-424
    • Mead, K.1    Macdonald, T.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.