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2004
Pyridine derivatives
R 0380
Tandem Overman Rearrangement and Intramolecular Amidomercuration ReacStereocontrolled Synthesis of cis- and trans-2,6-Dialkylpiperidines. — The
52- 122 tions.
Hg(II)-mediated reactions open an efficient and general route for the stereoselective
synthesis of trans- and cis-2,6-dialkylpiperidines from the readily available starting
allylic imidate (I). Its reaction with Hg(O-Tfa)2 in THF is trans-stereoselective, while
the N-protected carbamate (V) exhibits an excellent cis selectivity in the same reaction
in nitromethane. The trans- and cis- products (II) and (VI) are easily transformed into
solenopsin A and isosolenopsin A, respectively. — (SINGH, O. V.; HAN*, H.; Org.
Lett. 6 (2004) 18, 3067-3070; Dep. Chem., Univ. Tex., San Antonio, TX 78249, USA;
Eng.) — Steudel
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