TY - JOUR

T1 - Domino [4+1]-annulation of alpha,beta-unsaturated delta-amino esters with Rh(II)-carbenoids - a new approach towards multi-functionalized N-aryl pyrrolidines

AU - Medvedev, J.J.

AU - Galkina, O.S.

AU - Klinkova, A.A.

AU - Giera, D.S.

AU - Hennig, L.

AU - Schneider, C.

AU - Nikolaev, V.A.

PY - 2015

Y1 - 2015

N2 - Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate.

AB - Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate.

U2 - 10.1039/c4ob02454k

DO - 10.1039/c4ob02454k

M3 - Article

VL - 13

SP - 2640

EP - 2651

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -