Lewis acid catalyzed formal [3 + 2] cycloadditions of 1-azadienes with donor acceptor cyclopropanes to synthesize varieties of imine functionalized cyclopentanes and pyrrolidine derivatives in moderate to high yield have been developed. Moreover, pharmaceutically relevant azabicyclo[3.2.1] octane, bearing two all-carbon quaternary stereogenic centers at the bridgehead positions, has been synthesized by nosyl group deprotection and intramolecular amidation of imine functionalized cyclopentane derivative.
As traightforward and efficient method for the synthesiso fn itrogen-functionalized cyclopentane derivatives via [3+ +2] cycloaddition of enamines with donor-acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore,t he corresponding b-amino acid was synthesized by monodecarboxylation and hydrogenolysis.A nenantioenricheds ynthesis of nitrogen-functionalized cyclopentane derivatives throughd ynamic kinetic asymmetric transformation of racemic donor-acceptor cyclopropanes hasa lso been achieved employingac opper complex[ Cu(OTf) 2 -L1] as the catalyst affording an enantiomeric ratio up to 8:1.
An unexpected MgI 2 -promoted [2 + 4] cycloaddition reaction of in-situ generated 2-styrylmalonate from donor-acceptor cyclopropanes with chalconimines to synthesize highly substituted indenopyridine derivatives under the mild reaction conditions have been developed. Additionally, these derivatives were utilized for the synthesis of highly substituted 9-membered lactam by oxidative C=C bond cleavage and spiro [oxoindane-pyrrolidine] derivative via Meinwald type rearrangement.
An efficient method for the synthesis of spiro-cyclopentane benzofuran derivatives via a MgI2-catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes in good yield has been developed.
Reaction of the title substrates in the presence of MgI2 or Cu(O‐Tf)2 leads to an efficient preparation of various highly functionalized cyclopentanes, generally with good to excellent diastereoselectivity.
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