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. 2021 Jun 23;23(15):5503–5510. doi: 10.1039/d1gc01535d

Scope of DA reaction between 2-furoic acid derivatives (esters, amides) and maleimides under aqueous conditions.

graphic file with name d1gc01535d-u4.jpg
Entry X R2 3 Conv. 1a exo-3, % endo-3, % Isolatedb, %
1 OMe Me 3k 70 65 5 52(74)
2 OMe H 3l 67 65 2 43(64)/82c
3 OMe Et 3m 65 61 4 47(72)
4 OEt Me 3n 63 59 4 29(46)
5 OiPr Me 3o 54 50 4 26(49)
6 OtBu Me 3p 54 51 3 25(46)
7 NH2 Me 3q 94 91 3 77(83)
8 NMe2 Me 3r 81 77 4 41(51)
9 NHOH Me 3s 92 76 16 69(75)
a

Conversion determined from the 1H-NMR ratios of product isomers and starting material.

b

Isolated yield after (chromatographic) workup (in brackets, yield corrected on reacted starting material).

c

2 M initial concentration.