AN ASYMMETRIC TRANSFORMATION OF CYCLOHEXENE OXIDE TO (S)-2-CYCLOHEXEN-1-OL BY CHIRAL LITHIUM AMIDES
نویسندگان
چکیده
منابع مشابه
An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides
The mechanism of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amide was studied by quantum chemical calculations. The transition states of eight molecules were fully optimized at the ab initio HF/3-21G and density functional B3LYP/3-21G levels with Gaussian 98. The activation energies were calculated at the B3LYP/6-31+G(3df,2p)//B3LYP/3-21G l...
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The five-membered ring in the the title mol-ecule, C(24)H(25)NO, fused with the phenyl-ene ring, is almost planar (r.m.s. deviation = 0.023 Å), with the methyl-ene C atom deviating most from this mean plane [0.031 (1) Å]. The tertiary N atom shows a flattened pyramidal configuration [Σ(angles at N) = 350.3 (6)°].
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Highly efficient catalytic asymmetric [3 + 2] cycloadditions using a chiral copper amide are reported. Compared with the chiral CuOTf/Et3N system, the CuHMDS system showed higher reactivity, and the desired reactions proceeded in high yields and high selectivities with catalyst loadings as low as 0.01 mol %.
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Reaction of the chiral crystals of the achiral amides with n-butyllithium in toluene at -80 degrees C gave optically active alcohols in 17-84% ee.
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ژورنال
عنوان ژورنال: Chemistry Letters
سال: 1984
ISSN: 0366-7022,1348-0715
DOI: 10.1246/cl.1984.829