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Asymmetric diels-alder reactions catalyzed by chiral oxazaborolidines. Effect of the position of an electron-donor functionality in the α-side chain substituent on the enantioselectivity

1993; Elsevier BV; Volume: 34; Issue: 16 Linguagem: Inglês

10.1016/s0040-4039(00)77652-0

1873-3581

Jean-Paul G. Seerden, Hans W. Scheeren,

Traditional and Medicinal Uses of Annonaceae

Asymmetric Diels-Alder reactions of cyclopentadiene with methacrolein and 2-bromoacrolein catalyzed by chiral oxazaborolidines 1 derived from N-tosyl-L-α-amino acids afforded cycloadducts in quantitative yield. Variation in the position of an electron donor atom in the α-side chain substituent shows that enantioselectivity is controlled by the presence of electron donor atoms in position 2 and 4.