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Synthesis of N ‐Alkenylpurines by Rearrangements of the Corresponding N ‐Allyl Isomers: Scopes and Limitations
Author(s) -
Kania Jindrich,
Gundersen LiseLotte
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201455
Subject(s) - chemistry , stereoselectivity , selectivity , base (topology) , catalysis , stereochemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
N ‐9‐ and N ‐7‐alkenylpurines have been synthesized by rearrangement of the corresponding N ‐allyl derivatives, often in good yields and with high stereoselectivity. Base promoted and transition metal mediated rearrangements have been studied. Simple allylpurines were easily rearranged with catalytic amounts of RuClH(CO)(PPh 3 ) 3 . The efficiency of base promoted rearrangement was highly dependent on the detailed structure of the starting material, but this reaction often occurred with surprisingly high Z ‐selectivity.