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Volumn 38, Issue 10, 1999, Pages 1468-1470

Chelated enolates of amino acid esters - Efficient nucleophiles in palladium-catalyzed allylic substitutions

Author keywords

Alkylations; Allyl complexes; Amino acids; Enolates; Palladium

Indexed keywords

AMINO ACID DERIVATIVE; AMINO ACID ESTER; ENOLATE; ESTER DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

EID: 0033577898     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990517)38:10<1468::AID-ANIE1468>3.0.CO;2-O     Document Type: Article
Times cited : (108)

References (42)
  • 3
    • 0000276556 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford
    • Reviews: a) S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford, 1991, pp. 585-661;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 585-661
    • Godleski, S.A.1
  • 6
    • 0000273585 scopus 로고    scopus 로고
    • d) J. M. J. Williams, Synlett 1996, 705-710, and references therein.
    • (1996) Synlett , pp. 705-710
    • Williams, J.M.J.1
  • 34
    • 33747551758 scopus 로고    scopus 로고
    • note
    • Instead of the carbonate 3, the corresponding acetate or benzoate can be used as well. With the more reactive carbonates, the yields and selectivities are usually better. To avoid transesterifications by the liberated ethylate the tert-butyl ester should be used.
  • 35
    • 33747522633 scopus 로고    scopus 로고
    • note
    • 2 can be used as well. However, distinctly worse yields and selectivities are observed. In reactions of the lithium enolates (without addition of a chelating metal salt) N-allylated products can be isolated in addition to C-allylated products.
  • 38
    • 33747561506 scopus 로고    scopus 로고
    • note
    • However, a partial cleavage of the crotyl ester occurs.
  • 39
    • 33747561178 scopus 로고    scopus 로고
    • note
    • If the Pd-catalyzed allylation is carried out in the presence of LDA, product mixtures are usually formed due to the partial cleavage of the crotyl ester.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.