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Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene
Author(s) -
ElMansy Mohamed F.,
Sar Anobick,
Lindeman Sergey,
Donaldson William A.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203754
Subject(s) - cyclooctatetraene , phthalimide , heteroatom , optically active , nucleophile , bicyclic molecule , chemistry , carbon fibers , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , molecule , ring (chemistry) , materials science , catalysis , composite number , composite material
The racemic (6‐cyclo‐heptadienyl)Fe(CO) 3 + cation ((±)‐ 7 ), prepared from cyclooctatetraene, was treated with a variety of carbon and heteroatom nucleophiles. Attack took place at the less hindered C 1 dienyl carbon and decomplexation of the (cycloheptadiene)Fe(CO) 3 complexes gave products rich in functionality for further synthetic manipulation. In particular, a seven‐step route was developed from racemic (6‐styryl‐2,4‐cycloheptadien‐1‐yl)phthalimide ((±)‐ 9 d ) to afford the optically active aminocycloheptitols (−)‐ 20 and (+)‐ 20 .