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A New and Versatile Access to Polyazamacroheterocycles and Cryptands Through Ring‐Closing Bis(hydroaminomethylation)
Author(s) -
Kranemann Christian L.,
Eilbracht Peter
Publication year - 2000
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 - 10.1002/1099-0690(200007)2000:13<2367::aid-ejoc2367>3.0.co;2-t
Subject(s) - chemistry , cryptand , hydroformylation , ring (chemistry) , closing (real estate) , yield (engineering) , primary (astronomy) , combinatorial chemistry , organic chemistry , catalysis , rhodium , ion , materials science , political science , law , metallurgy , physics , astronomy
The Rh I ‐catalyzed hydroformylation of dienes in the presence of primary amines or secondary α,ω‐diamines has been applied to macroheterocyclic ring synthesis. Starting from (hetero)diallylic systems, 12‐ to 36‐membered polyheterocycles have been readily obtained in up to 56% yield. In addition, we show that the macrocyclic systems thus obtained can be debenzylated and that the resulting macrocyclic diamines undergo a second ring‐closing bis(hydroaminomethylation) to give cryptand systems.