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Synthesis and Structural Characterization of Novel Camphor‐derived Amines
Author(s) -
Grošelj Uroš,
Sevšek Alen,
Ričko Sebastijan,
Golobič Amalija,
Svete Jurij,
Stanovnik Branko
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22069
Subject(s) - chemistry , beckmann rearrangement , camphor , derivative (finance) , ketone , carbene , chirality (physics) , salt (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
Two novel 4‐substituted camphidine derivatives 10a , b have been prepared from (+)‐camphor ( 1 ) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b , formed as a side product during the hydrogenation of arylidene ketone 3b , under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12 . (1 S )‐(+)‐Camphorquinone ( 13 ) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17 , an N ‐heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X‐ray analysis. Chirality 24:778–788, 2012 . © 2012 Wiley Periodicals, Inc.