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Volumn 1995, Issue 7, 1995, Pages 737-738

Regio-and stereocontrolled iodocyclocarbamation of N -Carbamoyl-2,4-Dienylamine derivatives

Author keywords

1,4 functionalization of 1,3 diene; iodocyclocarbamation; N Carbamoyl 1 substituted 2,4 Dienylamine; trans oxazolidinone; hydroxy iodo homoallylamine

Indexed keywords


EID: 3042955482     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5073     Document Type: Article
Times cited : (7)

References (30)
  • 26
    • 85064658013 scopus 로고    scopus 로고
    • Carbamates la-c were prepared from l-substituted-2, 4-dienylamine (tricarbonyl)iron complexes4 by a two-step sequence of protection of the amino group and decomplexation of the Fe(CO)3 group, or vice versa. Id was obtained from a known compound, 1, 1-dimethylethyl 4-formyl-2, 2-dimethyl-3-oxazolidinecarboxylate (Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361), in 7 steps [(1) CH2CHCH2PPh3Br, KN(TMS)2; (2) p-TsOH, MeOH; (3) MOMC1, (i-Pr)2NEt; (4) BnBr, NaH; (5) CF3C02H; (6) MeOCOCl, K2C03; (7) 3N HC1, THF]
    • Carbamates la-c were prepared from l-substituted-2, 4-dienylamine (tricarbonyl)iron complexes4 by a two-step sequence of protection of the amino group and decomplexation of the Fe(CO)3 group, or vice versa. Id was obtained from a known compound, 1, 1-dimethylethyl 4-formyl-2, 2-dimethyl-3-oxazolidinecarboxylate (Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361), in 7 steps [(1) CH2CHCH2PPh3Br, KN(TMS)2; (2) p-TsOH, MeOH; (3) MOMC1, (i-Pr)2NEt; (4) BnBr, NaH; (5) CF3C02H; (6) MeOCOCl, K2C03; (7) 3N HC1, THF].
  • 27
    • 85064649522 scopus 로고    scopus 로고
    • Reaction with other iodonium reagents, such as N-iodosuccinimide and iodonium dicollidine perchlorate, resulted in low yield (10- 20%) and no stereoselectivity (2/3 = 1/1- 3/2)
    • Reaction with other iodonium reagents, such as N-iodosuccinimide and iodonium dicollidine perchlorate, resulted in low yield (10- 20%) and no stereoselectivity (2/3 = 1/1- 3/2).
  • 28
    • 85064693795 scopus 로고    scopus 로고
    • The addition of KI to the reaction mixture dramatically promoted both the reaction rate and the chemical yield without any loss of stereoselectivity
    • The addition of KI to the reaction mixture dramatically promoted both the reaction rate and the chemical yield without any loss of stereoselectivity.
  • 29
    • 85064592723 scopus 로고    scopus 로고
    • The relative stereochemistry of 2a-d and 3a-d was determined by NOE measurements of C4-H and vinylic proton (Cl'-H) or C4-H and C5-H, respectively
    • The relative stereochemistry of 2a-d and 3a-d was determined by NOE measurements of C4-H and vinylic proton (Cl'-H) or C4-H and C5-H, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.