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2005
Hydrogenated naphthalene derivatives
Q 1010
Reversal of Enantioselectivity on Protonation of Enol(ate)s Derived from
Using C2-Symmetric Sulfonamides. — The preparation of
16- 091 2-Methyl-1-tetralone
both enantiomers of tetralone (III) is envisaged using bis-sulfonamides (I) as the chiral
agents. The course of the reaction can be controlled by variation of the conditions. Best
results are obtained with agents (Ib) and (Id) and their bis-lithiated analogues. Quenching with Tms-Cl allows the removal of unreacted enolate as silyl enol ether (VI) to prevent in situ racemization. — (BOYD, E.; COUMBARIDES, G. S.; EAMES*, J.; HAY,
A.; JONES, R. V. H.; STENSON, R. A.; SUGGATE, M. J.; Tetrahedron Lett. 45
(2004) 51, 9465-9468; Dep. Chem., Queen Mary Westfield Coll., Univ. London,
London E1 4NS, UK; Eng.) — Lindner
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