Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene | Zendy

ElMansy Mohamed F. | Zendy; Sar Anobick | Zendy; Lindeman Sergey | Zendy; Donaldson William A. | Zendy

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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 .

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