European Journal of Organic Chemistry p. 2359 - 2366 (2012)
Update date:2022-08-02
Topics: Alcohols Catalyzed Three-component reaction Diastereoselective synthesis azetidine-2,3-diones
Alcaide, Benito
Almendros, Pedro
Aragoncillo, Cristina
Callejo, Ricardo
Ruiz, M. Pilar
Torres, M. Rosario
β-Lactam-oxindole hybrids have been synthesized in good yields in a one-pot procedure through efficient and stereoselective capture of an oxonium ylide with azetidine-2,3-diones. The reaction allows high to moderate control of stereoselectivity, depending on the 3-diazo-oxindole precursor and the hydroxylic compound used. Two new quaternary stereogenic centers were formed; the stereochemistry at the C-3 quaternary center was controlled by a bulky substituent at C-4, whereas the stereoselectivity in the adjacent second quaternary stereogenic center was controlled by the α-diazo-oxindole. The stereochemistry of both quaternary centers has been unambiguously assigned by single-crystal X-ray diffraction. Densely functionalized β-lactam-oxindole hybrids have been prepared in a one-pot, multicomponent reaction between azetidine-2,3-diones, α-diazo-oxindoles, and alcohols. Two new stereogenic centers were formed; the stereochemistry at the new C-3 quaternary center was controlled by a bulky substituent at C-4, whereas the second new stereogenic center was controlled by the α-diazo-oxindole.
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Doi:10.1080/00397911.2011.562336
(2012)Doi:10.1016/j.tetlet.2012.04.010
(2012)Doi:10.1016/j.bmcl.2012.03.103
(2012)Doi:10.1016/S0040-4020(01)81931-1
(1991)Doi:10.1006/jmre.2002.2596
(2002)Doi:10.1016/j.bmcl.2012.04.055
(2012)