TY - JOUR
T1 - Sugarometallic chemistry
T2 - Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction
AU - Shing, Tony K.M.
AU - Chow, Hak Fun
AU - Chung, Ivan H.F.
PY - 1996/5/2
Y1 - 1996/5/2
N2 - The diastereoselectivity of the Diels-Alder reaction of η6-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-β-L-arabinopyranoside) tricarbonylchromium(0) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was found to be R in each case.
AB - The diastereoselectivity of the Diels-Alder reaction of η6-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-β-L-arabinopyranoside) tricarbonylchromium(0) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was found to be R in each case.
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U2 - 10.1016/0040-4039(96)00648-X
DO - 10.1016/0040-4039(96)00648-X
M3 - Article
AN - SCOPUS:0029944030
SN - 0040-4039
VL - 37
SP - 3713
EP - 3716
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 21
ER -