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Volumn 17, Issue 11, 2006, Pages 1754-1757

Improved Schöllkopf construction of quaternary α-amino acids: efficient enantioselective synthesis of integrin LFA-1 antagonist BIRT-377

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; INTEGRIN; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1;

EID: 33745808337     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.06.019     Document Type: Article
Times cited : (17)

References (42)
  • 32
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    • For another enantioselective synthesis of BIRT-377 based on a highly diastereoselective alkylation of an aziridine-2-carboxylate ester, which appeared while this work was in progress, see:
    • For another enantioselective synthesis of BIRT-377 based on a highly diastereoselective alkylation of an aziridine-2-carboxylate ester, which appeared while this work was in progress, see:. Patwardhan A.P., Pulgram V.R., Zhang Y., and Wulff W.D. Angew. Chem., Int. Ed. 44 (2005) 6169-6172
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6169-6172
    • Patwardhan, A.P.1    Pulgram, V.R.2    Zhang, Y.3    Wulff, W.D.4
  • 34
    • 0019775816 scopus 로고
    • In sharp contrast to our results, Schöllkopf and coworkers have reported some time ago that alkylation of 1 with various electrophiles, using n-BuLi as the deprotonating base, is possible in good yields:
    • In sharp contrast to our results, Schöllkopf and coworkers have reported some time ago that alkylation of 1 with various electrophiles, using n-BuLi as the deprotonating base, is possible in good yields:. Schöllkopf U., Groth U., Westphalen K.-O., and Deng C. Synthesis (1981) 969-971
    • (1981) Synthesis , pp. 969-971
    • Schöllkopf, U.1    Groth, U.2    Westphalen, K.-O.3    Deng, C.4
  • 35
    • 33745858898 scopus 로고    scopus 로고
    • note
    • The enantiomer of 1 was prepared using ent-2 for HPLC comparison purpose which revealed 1 to be of >99% ee.
  • 39
    • 0032579180 scopus 로고    scopus 로고
    • For instance, 2 can be prepared conveniently from d-valine and alanine in a practical manner, see:
    • For instance, 2 can be prepared conveniently from d-valine and alanine in a practical manner, see:. Bull S.D., Davies S.G., and Moss W.O. Tetrahedron: Asymmetry 9 (1998) 321-327
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 321-327
    • Bull, S.D.1    Davies, S.G.2    Moss, W.O.3
  • 40
    • 33644941365 scopus 로고    scopus 로고
    • For a somewhat lengthy chiral-auxiliary-based approach to the synthesis of quaternary α-amino acid derivatives, which has been recently improved
    • For a somewhat lengthy chiral-auxiliary-based approach to the synthesis of quaternary α-amino acid derivatives, which has been recently improved. Roy S., and Spino C. Org. Lett. 8 (2006) 939-942
    • (2006) Org. Lett. , vol.8 , pp. 939-942
    • Roy, S.1    Spino, C.2
  • 42
    • 0030955088 scopus 로고    scopus 로고
    • For a highlight on new strategies to α,α-dialkylated α-amino acids, see:
    • For a highlight on new strategies to α,α-dialkylated α-amino acids, see:. Wirth T. Angew. Chem., Int. Ed. 36 (1997) 225-227
    • (1997) Angew. Chem., Int. Ed. , vol.36 , pp. 225-227
    • Wirth, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.