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2005
Bridged compounds
Q 0060
Grignard Reagent-Promoted Selective Ring Expansion and Alkylation of Formyl
and Isoborneol: A New Route to Highly Substituted Cyclopentanes. —
27- 071 Borneol
Treatment of formyl borneol with various Grignard reagents (II) results in a highly
selective ring expansion—alkylation reaction to give the products (III) (10 examples).
A mechanism for this reaction is proposed. The bicyclic compounds (III) can be converted into highly substituted chiral cyclopentanes such as (IV) and subsequently by
intramolecular aldol condensation into acyl bornylenes, e.g. (V). In contrast to (I),
reaction of formyl isoborneol (VI) with (IIa) forms the product (VII) of ring expansion
together with the alkylation product (VIII). — (YANG*, T.-F.; ZHANG, Z.-N.;
TSENG, C.-H.; CHEN, L.-H.; Tetrahedron Lett. 46 (2005) 11, 1917-1920; Dep. Appl.
Chem., Chaoyang Univ. Technol., Taichung 413, Taiwan; Eng.) — Roy
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