“…The dienophile precursor, 8 (Scheme 2), for the IMDA reaction was prepared from allylic bromide 10 10 by S N 2 displacement with p -methoxybenzylamine under conditions 11 (Cs 2 CO 3 , DMF) that select for the monoalkylated product (95%). Diene components – pentadienoic acid ( 7a ) 12 and commercially available sorbic acid ( 7b ) – were separately coupled with 8 and 9 to give tertiary amides 6a,b in good yields (73% and 80%, respectively).…”
The hexahydro-1H-isoindolin-1-one core of muironolide A was prepared by asymmetric intramolecular Diels Alder cycloaddition using a variant of the MacMillan organocatalyst which sets the C4,C5 and C11 stereocenters.
“…The dienophile precursor, 8 (Scheme 2), for the IMDA reaction was prepared from allylic bromide 10 10 by S N 2 displacement with p -methoxybenzylamine under conditions 11 (Cs 2 CO 3 , DMF) that select for the monoalkylated product (95%). Diene components – pentadienoic acid ( 7a ) 12 and commercially available sorbic acid ( 7b ) – were separately coupled with 8 and 9 to give tertiary amides 6a,b in good yields (73% and 80%, respectively).…”
The hexahydro-1H-isoindolin-1-one core of muironolide A was prepared by asymmetric intramolecular Diels Alder cycloaddition using a variant of the MacMillan organocatalyst which sets the C4,C5 and C11 stereocenters.
“…The use of aprotic solvents for N-alkylations has received considerable attention because of the interesting level of chemoselectivity and environmental compatibility as well as the simplicity of the procedure 18,19 . In this study, three solvents with different polarity were used to synthesize FTIR and GC analysis were carried out for the products prepared in those three solvents.…”
“…9,[13][14][15] In particular, selectively N-substituted putrescines and cadaverines present a challenge, since the available methods for di-and trimethylenediamines are not generally suitable for their higher homologues. Several preparations of N-alkyl tetra and pentamethylenediamines have already been described, [16][17][18] but very few general methods are available for N-aryl derivatives. [19][20][21] The literature regarding N-alkyl-N-arylputrescines and cadaverines 1 is even scarcer.…”
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