TY - JOUR
T1 - Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene
T2 - an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes
AU - Alonso, Inés
AU - Carretero, Juan C.
AU - García Ruano, José L.
AU - Martín Cabrejas, Luisa M.
AU - López-Solera, Isabel
AU - Raithby, Paul R.
PY - 1994/12/12
Y1 - 1994/12/12
N2 - The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl2 used.
AB - The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl2 used.
UR - http://www.scopus.com/inward/record.url?scp=0027941647&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)78571-6
DO - 10.1016/S0040-4039(00)78571-6
M3 - Article
AN - SCOPUS:0027941647
SN - 0040-4039
VL - 35
SP - 9461
EP - 9464
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 50
ER -