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Volumn 46, Issue 25, 2005, Pages 4403-4405

Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALKYL GROUP; AMINE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; IODINE; METAL DERIVATIVE;

EID: 19444372128     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.064     Document Type: Article
Times cited : (14)

References (19)
  • 10
    • 19444364537 scopus 로고    scopus 로고
    • note
    • The use of other solvents (DCM, toluene) required elevated temperatures (23-50°C) for the reaction to go to completion, and resulted in lower yields (88-95%)
  • 11
    • 19444385983 scopus 로고    scopus 로고
    • note
    • The major isomer was determined to have trans configuration by NOE experiments
  • 12
    • 19444381108 scopus 로고    scopus 로고
    • note
    • 3H (2 mol%) in toluene (7.5 mL/g vs 5) was added benzaldehyde dimethyl acetal (1.5 equiv) as a solution in toluene, slowly over 2 h. A mixture of methanol and toluene was distilled off over the course of the reaction under slight vacuum (200 Torr) to minimize esterification of the carbamate starting material. Toluene was continually added through the distillation to maintain the approximate starting volume
  • 13
    • 19444379775 scopus 로고    scopus 로고
    • note
    • The de was determined at methyl ester 8b via SFC (Chiralcel OF column)
  • 14
    • 19444384026 scopus 로고    scopus 로고
    • note
    • and were identified by LCMS of the crude reaction mixture of 7 with iodine in MeOH
  • 16
    • 19444362540 scopus 로고    scopus 로고
    • note
    • In a simplified system, water acidified to pH 1, 2, 3, and 5 by aqueous HCl was used in the iodocyclization deprotection of Alloc-phenylglycine methyl ester. The reaction was monitored by HPLC over 24 h. No noticeable differences were observed between the reactions
  • 17
    • 19444376278 scopus 로고    scopus 로고
    • note
    • 2 (3 × 15 mL). The organic and aqueous layers were quantitatively assayed by HPLC for product


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.