Allylic protection of thiols and cysteine: I: The allyloxycarbonylaminomethyl group

Tetrahedron

Volumn 55, Issue 22, 1999, Pages 6931-6944

  Kimbonguila, André Malanda ^a   Merzouk, Ahmed ^a   Guibé, François ^a   Loffet, Albert ^b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b Senn Chemicals International   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYSTEINE; METHYL GROUP; PALLADIUM; THIOL; THIOL DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; DECOMPOSITION; LYSIS; PRIORITY JOURNAL; PROTECTION; SYNTHESIS;

EID: 0033612121     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00322-1     Document Type: Article

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16. 3, as the allyl group scavenger were not only unsuccessful but completely inhibited the rearrangement of allyl carbamates into allylamines. On another hand, it should be noted that palladium catalysed allylation of trimethylsilyl derivatives of thiols is possible when allyl carbonic esters or epoxides which are much better π-allyl palladium precursors under Tsuji-Trost conditions than allyl carbamates are used as allylating agents (see: Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141-4144; see also: Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc. Chem. Commun. 1986, 146-147).
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