Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2575-2578

  Yang, Qifei ^a   Ney, Joshua E ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PHOSPHINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINATION; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; PALLADIUM; PHOSPHINES; PYRROLIDINES; STEREOISOMERISM;

EID: 27544506294     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050647u     Document Type: Article

References (26)

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22. BINAP = 2,2′-diphenylphosphino-1,1′-binaphthyl, dppe = 1,2-bis-(diphenylphosphino)ethane, dpe-phos = bis(2-diphenylphosphinophenyl)- ether.
23. 3/2-catalyzed reaction of 5-(N-phenylamino)-1,8-nonadiene with 2-bromonaphthalene afforded only 41% isolated yield of the desired 2,5-disubstituted pyrrolidine.
24. Small amounts (ca. 5-10%) of 2-methyl-3-arylpyrrolidine derivatives were also formed in some of these transformations. See Supporting Information for further details.
25. 1H NMR NOE experiments or by comparison of spectra to related compounds of known configuration. See Supporting Information for further details.
26. Use of BINAP in the second step of the tandem reaction led to the formation of increased amounts of N,N-diarylamino alkenes bearing two different N-aryl substituents.