메뉴 건너뛰기




Volumn 10, Issue 19, 2008, Pages 4347-4350

Diastereoselective Synthesis of α,β′-Disubstituted Aminomethyl(2-carboxyethyl)phosphinates as Phosphinyl Dipeptide Isosteres

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; PHOSPHINIC ACID DERIVATIVE;

EID: 55449110051     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801743d     Document Type: Article
Times cited : (21)

References (33)
  • 15
    • 39849090312 scopus 로고    scopus 로고
    • The method to separate inidividual phosphinic dipeptide stereoisomers using HPLC was reported, see
    • The method to separate inidividual phosphinic dipeptide stereoisomers using HPLC was reported, see: Mucha, A.; Lammerhofer, M.; Lindner, W.; Pawelczak, M.; Kafarski, P. Bioorg. Med. Chem. Lett. 2008, 18, 1550.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 1550
    • Mucha, A.1    Lammerhofer, M.2    Lindner, W.3    Pawelczak, M.4    Kafarski, P.5
  • 17
    • 34447102681 scopus 로고    scopus 로고
    • For application of our methodology to the synthesis of α,α′-diaminophosphinates and α-amino-α′- hydroxyphosphinates, see: a
    • For application of our methodology to the synthesis of α,α′-diaminophosphinates and α-amino-α′- hydroxyphosphinates, see: (a) Kaboudin, B.; Haruki, T.; Yamagishi, T.; Yokomatsu, T. Tetrahedron 2007, 63, 8199.
    • (2007) Tetrahedron , vol.63 , pp. 8199
    • Kaboudin, B.1    Haruki, T.2    Yamagishi, T.3    Yokomatsu, T.4
  • 20
    • 0031032162 scopus 로고    scopus 로고
    • Alkylation of lithiun enolates derived from γ-amino esters and δ-hydroxy esters was reported to proceed with high diastereoselectivity. In these cases, selectivity were rationalized by cis-enolates bearing a cyclic chelated structure. Reactions of γ-amino esters: (a) Hanessian, S, Schaum, R. Tetrahedron Lett. 1997, 38, 163
    • Alkylation of lithiun enolates derived from γ-amino esters and δ-hydroxy esters was reported to proceed with high diastereoselectivity. In these cases, selectivity were rationalized by cis-enolates bearing a cyclic chelated structure. Reactions of γ-amino esters: (a) Hanessian, S.; Schaum, R. Tetrahedron Lett. 1997, 38, 163.
  • 22
    • 61349128569 scopus 로고    scopus 로고
    • Reactions of δ-hydroxy esters: (c) Narasaka, K.; Ukaji, Y. Chem. Lett. 1986, 59, 81.
    • Reactions of δ-hydroxy esters: (c) Narasaka, K.; Ukaji, Y. Chem. Lett. 1986, 59, 81.
  • 26
    • 0026026733 scopus 로고    scopus 로고
    • A similar benzylation of 14 was also attempted using LiCl (6 equiv) as an additive, which has previously been elucidated to enhance the reactivity of lithium enolates and have an influence on the diastereoselectivity of their alkylation reactions by changing the aggregated states. However, the selectivity was deteriorated to 21a:21b = 3:1. For LiCl-mediated reactions of lithium enolates with electrophiles, see: (a) Seebach, D.; Grundler, H.; Shoda, S.-I. Helv. Chim. Acta 1991, 74, 197.
    • A similar benzylation of 14 was also attempted using LiCl (6 equiv) as an additive, which has previously been elucidated to enhance the reactivity of lithium enolates and have an influence on the diastereoselectivity of their alkylation reactions by changing the aggregated states. However, the selectivity was deteriorated to 21a:21b = 3:1. For LiCl-mediated reactions of lithium enolates with electrophiles, see: (a) Seebach, D.; Grundler, H.; Shoda, S.-I. Helv. Chim. Acta 1991, 74, 197.
  • 33
    • 0003014574 scopus 로고    scopus 로고
    • 2-mediated removal of the sulfonyl group of N-benzoyl benzenesulfonamide derivatives, see: Knowles, H.; Parsons, A. F.; Pettifer, R. M. Synlett. 1997, 271.
    • 2-mediated removal of the sulfonyl group of N-benzoyl benzenesulfonamide derivatives, see: Knowles, H.; Parsons, A. F.; Pettifer, R. M. Synlett. 1997, 271.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.