866492-46-8Relevant articles and documents
First [4 + 2] cycloadditions involving the olefinic bond of an 'aldoketeniminium salt' (= N-alk-1-enylideneaminium salt)
Mahuteau-Betzer, Florence,Ding, Ping-Yu,Ghosez, Leon
, p. 2022 - 2031 (2005)
Keteniminium triflates' (= N-alk-1-enylideneaminium trifluoromethanesulfonates; [MeN(Ts)CH=C= NR1(R2)] +TfO-) generated in situ from Nα- tosylsarcosinamides MeN(Ts)CH2CONR1(R2) unexpectedly react with cyclopenta-1,3-diene and cyclohexa-1,3-diene to give Diels-Alder reactions across the C=C bond of the cumulene. The use of N α-tosylsarcosinamides derived from chiral pyrrolidines allows the direct preparation of trinorbornenone derivative 6 in high enantiomer purity.