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2004
Pyridine derivatives
R 0380
Synthesis of Functionalized 1-Azaspirocyclic Cyclopentanones Using Broensted
or N-Bromosuccinimide Promoted Ring Expansions. — A variety of 6-aza51- 111 Acid
spiro[4.5]decan-1-ones are prepared through semipinacol ring expansion reactions of
hydroxycyclobutanes. Reactions promoted by NBS give higher yields and proceed with
greater diastereoselectivity compared to those reactions promoted by HCl or CSA.
Interestingly, the reactions of substrates (V) using either an acid or NBS afford complementary diastereomers with respect to the newly formed spirocyclic carbon atom
and the substituent at the 4-position of the pyridine ring. — (DAKE*, G. R.;
FENSTER, M. D. B.; HURLEY, P. B.; PATRICK, B. O.; J. Org. Chem. 69 (2004) 17,
5668-5675; Dep. Chem., Univ. British Columbia, Vancouver, B. C. V6T 1Z1, Can.;
Eng.) — Klein
2004
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