The problem of the synthesis of trans-1,4-disubstituted hydrazino and amino cyclopentenes has been resolved by a sequential copper-catalyzed rearrangement-allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes. The cis-fused 5,5-membered allylic carbazate which is formed in situ by a novel Cu(OTf)2/(±)-binap catalyzed rearrangement, can be alkylated with a broad spectrum of Grignard reagents with a predominant SN2’-regioselectivity. N-Boc protecting group proved to be optimal as regards yields, reaction times and regioselectivities

Sequential Copper-Catalyzed Rearrangement-Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents

PINESCHI, MAURO
2009

Abstract

The problem of the synthesis of trans-1,4-disubstituted hydrazino and amino cyclopentenes has been resolved by a sequential copper-catalyzed rearrangement-allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes. The cis-fused 5,5-membered allylic carbazate which is formed in situ by a novel Cu(OTf)2/(±)-binap catalyzed rearrangement, can be alkylated with a broad spectrum of Grignard reagents with a predominant SN2’-regioselectivity. N-Boc protecting group proved to be optimal as regards yields, reaction times and regioselectivities
F., Bertolini; S., Crotti; F., Macchia; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/129049
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