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Synthesis of Nitrogen‐Containing Spiro Compounds from Lactams by Allylboration and Subsequent Ring‐Closing Metathesis

“…2,2‐Diallyl‐1‐benzylpiperidine (3a): Prepared according to the literature procedure 11 . 1 H NMR (CDCl 3 , ppm): δ = 1.47−1.62 (m, 6 H, C H 2 cyclic), 2.16 (dd, J = 14.4, 7.8 Hz, 2 H, H 2 C=CHC H H), 2.48 (pseudo t, J app = 5.4 Hz, 2 H, C H 2 N), 2.66 (dd, J = 14.4, 7.2 Hz, 2 H, H 2 C=CHCH H ), 3.66 (s, 2 H, C H 2 Ph), 5.06−5.15 (m, 4 H, CH=C H 2 ), 6.00 (ddt, J = 15.9, 11.1, 7.5 Hz, 2 H, C H =CH 2 ), 7.21−7.42 (m, 5 H, C 6 H 5 ).…”

“…In this publication, we present a straightforward route to 6‐azaspiro[4. n ]alkenes starting from commercially available lactams by allylboration of the carbonyl carbon atoms followed by ring‐closing metathesis of the obtained diallyl derivatives 11…”

The chemistry of the carbon–transition metal double and triple bond: annual survey covering the year 2002

“…84) for synthesis of dihydroxyproline [276] and swainsonine [277]; (5) formation of cyclic amino acids [278]; (6) formation of six-membered ring cyclic lactams (e.g. 85) for total synthesis of lentiginosine [279]; (7) formation of tetrahydropyridine derivatives [280,281]; (8) asymmetric formation of tetrahydropyridine derivatives [282]; (9) formation of tetrahydropyridine derivatives for total synthesis of aspidosperma alkaloids [283]; (10) formation of 9-azabicyclo[3.3.1]nonane derivatives (e.g. 86) for total synthesis of adaline [284]; (11) formation of methylenedihydropyridines (e.g.…”