Abstract
N -Methylisoxazolidines are formed
in good yields and high regio-, diastereo- and enantioselectivity
via asymmetric 1,3-dipolar cycloaddition of nitrones with enals
catalyzed by a chiral ruthenium Lewis acid. Electronic effects in
the dipole are the key to activation of these substrates for efficient
catalysis.
Key words
asymmetric catalysis - Lewis acid - ruthenium -
N -methyl nitrones - 1,3-dipolar
cycloaddition
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Optimization of the reaction conditions
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to be the optimal temperature for this combination of substrates
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nondried, undistilled, commercial grade solvents. The same results
as above were obtained with THF and EtOAc. Lower yields (60%)
and selectivities were obtained when using CHCl3 (>95:5 endo /exo ,
81% ee) or toluene (84:16 endo /exo , 90% ee). Alcohols, DMF,
DMSO, or acetone led to extensive decomposition of the nitrone.
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