Chiral auxiliaries in asymmetric Diels-Alder reaction

Sudo and Saigo153 reported the application of ds-2-amino-3,3-dimethyl-l-indanol derived l,3-oxazolidin-2-one 231 as a chiral auxiliary in asymmetric Diels-Alder reactions. The TV-crotonyl and TV-acryloyl derivatives were reacted with cyclopentadiene, 1,3-cyclohexadiene, isoprene and 2,3-dimethyl-l,3-butadiene, using diethylaluminum chloride as the Lewis acid catalyst. The reactions afforded the expected cycloadducts in moderate to high yields (33-97%) with high endo selectivities and high de values (92% to >98%). 

Shing, T K M, Chow, H E, Chung, IH E, Sugarometallic chemistry aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction. Tetrahedron Lett., 37, 3713-3716, 1996. Akiyama, T, Horiguchi, N, Ida, T, Ozaki, S, Stereodivergent Diels-Alder reactions employing cyclitols as chiral auxiliaries, Chem. Lett., 975-976, 1995. 

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See also in sourсe #XX -- [ , ]

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