First [4+2] cycloadditions involving the olefinic bond of an 'aldoketeniminium salt' (= N-alk-1-enylideneaminium salt)
(2005) Helvetica Chimica Acta — Vol. 88, n° 7, p. 2022-2031 (2005)
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- Abstract
- 'Keteniminium triflates' (=N-alk-1-enylideneaminium trifluoromethanesulfonates; [MeN(Ts)CH=C= NR1(R-2)]+TfO-) generated in situ from N-alpha-tosylsarcosinamides MeN(Ts)CH2CONR1(R-2) unexpectedly react with cyclopenta-1,3-diene and cyclohexa-1,3-diene to give Diets-Alder reactions across the C=C bond of the cumulene. The use of N-alpha-tosylsarcosinamides derived from chiral pyrrolidines allows the direct preparation of trinorbornenone derivative 6 in high enantiomer purity.
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Mahuteau-Betzer, F., Ding, P.-Y., & Ghosez, L. (2005). First [4+2] cycloadditions involving the olefinic bond of an ‘aldoketeniminium salt’ (= N-alk-1-enylideneaminium salt). Helvetica Chimica Acta, 88(7), 2022-2031. https://doi.org/10.1002/hlca.200590154 (Original work published 2005)