TY - JOUR
T1 - Regio- and π-facial selective Lewis acid interceded Diels-Alder reactions of α-dienyl-β-lactams
T2 - an indepth analysis
AU - Bhargava, Gaurav
AU - Anand, Amit
AU - Mahajan, Mohinder P.
AU - Saito, Takao
AU - Sakai, Ken
AU - Medhi, Chitrani
PY - 2008/7/7
Y1 - 2008/7/7
N2 - The regio-, diastereo-, and π-facial selective Lewis acid mediated Diels-Alder reactions of cis/trans-3-butadienyl-2-azetidinones with unsymmetrical dienophiles viz. methyl acrylate, dimethyl fumarate, and acrolein leading to the synthesis of diastereomerically pure and biologically potent 1,3,4-trisubstituted-2-azetidinones are reported. Theoretical calculations at HF/6-31G** and 6-31G**/DFT levels have been performed to support the observed π-facial selectivity. The formation of diastereomerically pure 'endo' adducts is supported by the X-ray diffraction studies.
AB - The regio-, diastereo-, and π-facial selective Lewis acid mediated Diels-Alder reactions of cis/trans-3-butadienyl-2-azetidinones with unsymmetrical dienophiles viz. methyl acrylate, dimethyl fumarate, and acrolein leading to the synthesis of diastereomerically pure and biologically potent 1,3,4-trisubstituted-2-azetidinones are reported. Theoretical calculations at HF/6-31G** and 6-31G**/DFT levels have been performed to support the observed π-facial selectivity. The formation of diastereomerically pure 'endo' adducts is supported by the X-ray diffraction studies.
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U2 - 10.1016/j.tet.2008.04.087
DO - 10.1016/j.tet.2008.04.087
M3 - Article
AN - SCOPUS:45449085010
SN - 0040-4020
VL - 64
SP - 6801
EP - 6808
JO - Tetrahedron
JF - Tetrahedron
IS - 28
ER -