TY - JOUR
T1 - Camphor-derived alcohols as chiral auxiliaries for asymmetric Pauson-Khand bicyclizations. Enantioselective synthesis of α-methoxyenones
AU - Verdaguer, Xavier
AU - Moyano, Albert
AU - Pericàs, Miquel A.
AU - Riera, Antoni
AU - Greene, Andrew E.
AU - Piniella, Joan F.
AU - Alvarez-Larena, Angel
PY - 1992/7/28
Y1 - 1992/7/28
N2 - The intramolecular Pauson-Khand reaction of enol and ynol ethers of Oppolzer's camphor-derived neopentyloxy alcohols is described. Bicyclic products are obtained in yields of up to 65% and with diastereoselectivities as high as 94:6 under very mild reaction conditions. The absolute configurations of the major stereoisomers obtained when (1R, 2S, 3R, 4S)-3-neopentyloxy-1,7,7-trimethylbicyclo- [2.2.1]heptan-2-ol is used as a chiral auxiliary are rationalized on the basis of the theoretically predicted preferential conformations of model precursors. A simple procedure for obtaining auxiliary-free, enantiopure bicyclic α-methoxyenones is also presented. © 1992.
AB - The intramolecular Pauson-Khand reaction of enol and ynol ethers of Oppolzer's camphor-derived neopentyloxy alcohols is described. Bicyclic products are obtained in yields of up to 65% and with diastereoselectivities as high as 94:6 under very mild reaction conditions. The absolute configurations of the major stereoisomers obtained when (1R, 2S, 3R, 4S)-3-neopentyloxy-1,7,7-trimethylbicyclo- [2.2.1]heptan-2-ol is used as a chiral auxiliary are rationalized on the basis of the theoretically predicted preferential conformations of model precursors. A simple procedure for obtaining auxiliary-free, enantiopure bicyclic α-methoxyenones is also presented. © 1992.
U2 - 10.1016/0022-328X(92)80156-R
DO - 10.1016/0022-328X(92)80156-R
M3 - Article
VL - 433
SP - 305
EP - 310
IS - 3
ER -