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Volumn 50, Issue 3, 2009, Pages 333-336

Diastereoselective electrophilic α-amination of camphor N1-acyl N2-phenylpyrazolidinones: the metal enolate-dependent synthesis of two possible hydrazide diastereomers

Author keywords

Amination; Chiral auxiliary; Reversal of stereoselectivity

Indexed keywords

1 N ACYLPYRAZOLIDINONE DERIVATIVE; 2 N PHENYLPYRAZOLIDINONE DERIVATIVE; AMIDE; ELECTROPHILE; HYDRAZIDE; LITHIUM DERIVATIVE; LITHIUM HEXAMETHYLDISILYLAMIDE; POTASSIUM DERIVATIVE; POTASSIUM HEXAMETHYLDISILYLAMIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57149132089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.003     Document Type: Article
Times cited : (11)

References (40)
  • 1
    • 4544359931 scopus 로고    scopus 로고
    • For recent reviews, see:
    • For recent reviews, see:. Erdik E. Tetrahedron 60 (2004) 8747-8782
    • (2004) Tetrahedron , vol.60 , pp. 8747-8782
    • Erdik, E.1
  • 37
    • 57149145499 scopus 로고    scopus 로고
    • note
    • 1H NMR studies of 2a showed that the conformeric ratio increases with increasing temperature. For example, the conformeric ratio of hydrazide 2a is 1.5 when the spectrum was recorded at -15 °C. The ratio was increased to 1.7 (at 5 °C), to 1.9 (at 25 °C) and further to 2.3 (at 55 °C). Interestingly, a third conformer appears when the temperature was decreased to -55 °C.
  • 40
    • 57149142115 scopus 로고    scopus 로고
    • note
    • The absolute stereochemistry of the minor (S)-α-amino diastereomer 6 was confirmed by single crystallographic X-ray analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.