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Volumn 74, Issue 10, 2009, Pages 3936-3939

Fluoride ion and phosphines as nucleophilic catalysts: Synthesis of 1,4-benzothiazepines from cyclic sulfenamides

Author keywords

[No Author keywords available]

Indexed keywords

ATOM ECONOMY; CHEMICAL EQUATIONS; ELECTRON-DEFICIENT; ENANTIOPURE; FLUORIDE ION; HIGH EFFICIENCY; SULFENAMIDE; SULFENAMIDES;

EID: 65949088576     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900449a     Document Type: Article
Times cited : (21)

References (60)
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    • The molecular structure of 3a was confirmed by X-ray crystallographic analysis (see Supporting Information). Interestingly, two conformations were positioned in the unit cell: either the iso-propyl group is in a pseudoequatorial or is in a pseudoaxial disposition, as in the molecular structures of sulfenamides 1a and 1c.
    • The molecular structure of 3a was confirmed by X-ray crystallographic analysis (see Supporting Information). Interestingly, two conformations were positioned in the unit cell: either the iso-propyl group is in a pseudoequatorial or is in a pseudoaxial disposition, as in the molecular structures of sulfenamides 1a and 1c.
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    • 2 at 40 °C, less than 10% of conversion was observed.
    • 2 at 40 °C, less than 10% of conversion was observed.
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    • 3a was obtained in 99% ee (Chiral HPLC, Daicel AD).
    • 3a was obtained in 99% ee (Chiral HPLC, Daicel AD).
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    • Bis(arylsulfonyl)acetylenes were not used due to their instability at room temperature
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    • 19F NMR but, due to problems of solubility, no characteristics signal has been found.
    • 19F NMR but, due to problems of solubility, no characteristics signal has been found.
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    • The corresponding thiosulfinate was not observed.
    • The corresponding thiosulfinate was not observed.
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    • Fifty-five percent of starting material 1a was recovered.
    • Fifty-five percent of starting material 1a was recovered.
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    • However, the fluoride ion has been reported as catalyst, in a desilylation-defluorination sequence
    • However, the fluoride ion has been reported as catalyst, in a desilylation-defluorination sequence: Uneyama, K. J. Fluorine. Chem. 2007, 128, 1087.
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    • 3CN (rt to 80 °C).
    • 3CN (rt to 80 °C).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.