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2004
Enantioselective syntheses
O 0031
Evaluation of (+)-Sparteine-Like Diamines for Asymmetric Synthesis. — The
(+)-sparteine surrogate (Ia) and three new analogues (Ib)—(Id) are tested in two
52- 023 known
different reactions, the α-lithiation rearrangement of cyclooctene oxide and the oxidative kinetic resolution of 1-indanol. Diamines (I) exhibit enantioselectivity opposite to
that observed with (—)-sparteine. From the present and previously reported results it
is concluded that diamine (Ia) is the most useful (+)-sparteine surrogate today. It is applied with much success in four other reactions, but fails in the attempted dynamic resolution of lithiated borane (XVI). — (DEARDEN, M. J.; MCGRATH, M. J.;
O'BRIEN*, P.; J. Org. Chem. 69 (2004) 17, 5789-5792; Dep. Chem., Univ. York,
Heslington, York YO10 5DD, UK; Eng.) — Klein
2004
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