A nucleophilic addition ring closure [NARC]-based synthesis of (+) -nonactic acid

Author(s):  
Benjamin Fraser ◽  
Patrick Perlmutter
2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
N. F. Kirillov ◽  
E. A. Nikiforova ◽  
D. V. Baibarodskikh ◽  
T. A. Zakharova ◽  
L. S. Govorushkin

Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).


ChemInform ◽  
2003 ◽  
Vol 34 (20) ◽  
Author(s):  
Benjamin Fraser ◽  
Patrick Perlmutter

1984 ◽  
Vol 62 (11) ◽  
pp. 2451-2455 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis

The reactivity of the epoxy-fulvene 1, prepared by pyrrolidine catalyzed condensation of cyclopentadiene and epoxybutanone, has been examined with various nucleophiles. It is a versatile intermediate for the preparation of spiro[2.4]hepta-4,6-diene synthons via nucleophilic addition to the C6 position of the fulvene followed by intramolecular cyclization of the substituted cyclopentadiene anion generated insitu.


2004 ◽  
Vol 6 (6) ◽  
pp. 893-895 ◽  
Author(s):  
Giang Nguyen ◽  
Patrick Perlmutter ◽  
Mark L. Rose ◽  
Filisaty Vounatsos

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