Imino Diels-Alder reactions have been investigated as a new route to sparteine analogues. The first enantioselective synthesis of two diastereoisomeric tricyclic diamines, structurally equivalent to the ABC and BCD rings of the naturally occurring alkaloid, is reported, starting from enantiopure intermediates. The effectiveness of the diamines in the lithiation of N-Boc-pyrrolidine is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
Synthesis of enantiopure diamine ligands related to sparteine, via scandium triflate-catalyzed imino Diels-Alder reactions / B. Danieli, G. Lesma, D. Passarella, P. Piacenti, A. Sacchetti, A. Silvani, A. Virdis. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 43:40(2002), pp. 7155-7158.
Synthesis of enantiopure diamine ligands related to sparteine, via scandium triflate-catalyzed imino Diels-Alder reactions
B. DanieliPrimo
;G. LesmaSecondo
;D. Passarella;A. SilvaniPenultimo
;
2002
Abstract
Imino Diels-Alder reactions have been investigated as a new route to sparteine analogues. The first enantioselective synthesis of two diastereoisomeric tricyclic diamines, structurally equivalent to the ABC and BCD rings of the naturally occurring alkaloid, is reported, starting from enantiopure intermediates. The effectiveness of the diamines in the lithiation of N-Boc-pyrrolidine is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
